Monthly Rentals in Siesta Key

(103 rentals)

Looking for a tropical getaway on Florida’s Gulf Coast? Our monthly rentals in Siesta Key offer the perfect long-term escape in one of the most beautiful beach destinations in the world. Whether you're planning a winter retreat or a summer vacation, Siesta Key’s pristine beaches, vibrant nightlife, and outdoor activities make it an ideal destination.

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Siesta Key Townhome
3 BR | 3.5 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 3.5 bathrooms
5 reviews

Distance to beach: 0.3 miles to Crescent Beach

$396

avg/night

$396
avg per night
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Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Beautiful and stylish townhouse style condo three level unit with 3 main bedrooms plus a bonus bath and laundry and bedroom on the ground floor. Each bedroom has a queen bed, and all furniture and mattresses were purchased new in 2021. New AC and duct work in 2023. Brand new exterior paint and roof ...

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Property Type

Siesta Key Townhome

Featured review

"Best vacation ever!!"

We cant say enough about how beautiful this townhouse was, fully stocked with everything, (the blender was great to have because we love our mudslides out by the private pool) The location was unbelievable, ...

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Siesta Key Condo
2 BR | 2 BA | Sleeps 5 | Quick View
Sleeps 5, 2 bedrooms, 2 bathrooms
5 reviews

Distance to beach: 100 feet to Crescent Beach

$380

avg/night

$380
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Private pool
  • WiFi

About this property

Relax and listen to the waves while sitting on your private lani. You're on the top floor (6th) of the Siesta Breakers Condominium, a private, gated facility with direct access to Crescent Beach, the #1 Top Rated beach in the USA.This luxury 2 bedroom 2 bath apartment, has been kept up to date ...

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Property Type

Siesta Key Condo

Featured review

"Perfect"

Siesta Breakers is the perfect place to get away. This condo was wonderful and had everything we needed! You couldn’t ask for more beauty, comfort, and relaxation! This is the perfect place.

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Siesta Key Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms
3 reviews

$314

avg/night

$314
avg per night
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Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Enjoy our 2br 2 bathroom ground floor condo. 30’ to the pool, tennis courts, Weber gas grills, and picnic table . Or cross the street to private deeded beach access on the #1 beach in the US. Enjoy bayside fishing on the fishing deck. 1280 square feet of living space. Roku tv’s and ...

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Property Type

Siesta Key Condo

Featured review

"Million dollar view"

Great condo, good location, loved the beach! The only thing that wasn't perfect was the weather. We are coming back at a different time.

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Siesta Key Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms
8 reviews

Distance to beach: 0.2 miles to Siesta Key

$258

avg/night

$258
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • Rentals by owner
  • WiFi

About this property

NEWLY REMODELED - LUXURY WATERVIEW CONDO FOR COUPLES or Families GETAWAY - POOLS, GYM, TENNIS - Walk to beach, town, shopping, top restaurants, live music, and entertainment.Walk out of the front door of this fantastic condo, grab your beach gear and take a short walk and you'll hit the beach ...

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Property Type

Siesta Key Condo

Featured review

"Great place!"

This was our first time back to Siesta Key in 20 years and we loved this condo! The location is right between the two villages, so super easy to grab a trolly to dine or shop. The beach is a pretty short ...

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Siesta Key Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms
26 reviews

Distance to beach: 0.1 miles to Siesta Key Beach

$170

avg/night

$170
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

NEWLY UPGRADED - BEAUTIFUL CONDO FOR THE PERFECT GETAWAY FROM THE COLD Right across from Siesta Key Beach, minutes from Siesta Key Village - or the South Village - shopping, top restaurants, live music, and entertainment. Walk , bike or take the free trolley.Sit on the balcony for a quiet and ...

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Property Type

Siesta Key Condo

Featured review

"Spectacular Vacation"

My husband and I booked this perfect condo in a wonderful location. The condo was spacious, comfortable and beautifully decorated. The beautiful sandy beach was right across the road. We enjoyed hanging ...

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Siesta Key House
3 BR | 3 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 3 bathrooms

$412

avg/night

$412
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

The front of the home has a privacy wall with a beautifully landscaped private courtyard for seating , sun bathing , relaxing & grilling. This Canal Home has a very large Heated Pool and Spa with a large limestone deck area. Only a one minute walk to Siesta Key Village where you can enjoy the shops, ...

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Property Type

Siesta Key House

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Siesta Key Townhome
3 BR | 3 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 3 bathrooms
8 reviews

Distance to beach: 0.3 miles to Crescent Beach

$427

avg/night

$427
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Discover the ultimate Siesta Key getaway with this beautifully appointed 3-bedroom condo, perfectly situated just 300 steps from the world-famous Crescent Beach. Enjoy the best of both worlds with Turtle Beach only 2.4 miles away, offering endless opportunities for seaside relaxation and adventure and ...

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Property Type

Siesta Key Townhome

Featured review

"Paradise!"

The place was immaculate and had everything we needed. It was so nice to have beach towels, chairs, and sand toys provided. The location is perfect. It's a very short walk to the beach. Some restaurants ...

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Siesta Key House
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms

Distance to beach: 0.7 miles to Siesta Key Beach

$823

avg/night

$823
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Hard to find home near #1 Siesta Key Beach and Village with all the amenities. The space Welcome to island life!Luxurious 3 bed/2 bath with spectacular water view and walking distance to the village restaurants, shopping, and #1 beach in America!Enjoy your heated pool, fire pit, and fishing ...

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Property Type

Siesta Key House

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Siesta Key House
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms
8 reviews

$669

avg/night

$669
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Rentals by owner
  • WiFi

About this property

Take it easy at this mid-century modern peaceful Siesta Key Beach family & pet friendly getaway. 3 BD, 2 BA’s & 2 outdoor showers to wash off the sand after beach fun. Don’t forget to bring Fido! Hang out by the fire pit in the evenings while you grill out taking in the ocean air with ...

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Property Type

Siesta Key House

Featured review

"Paradise"

The home on Siesta Key is totally amazing in every aspect. The completely updated modern architecture combined with the lush tropical landscape make this an excellent choice to relax and experience ...

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Siesta Key Condo
1 BR | 1 BA | Sleeps 3 | Quick View
Sleeps 3, 1 bedroom, 1 bathroom
10 reviews

Distance to beach: 0.5 miles to Siesta Key Main Beach

$109

avg/night

$109
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Sweet and spacious one bedroom condo in a Siesta Key Luxury Resort Building - Harbor Towers Yacht & Racquet Club. Great view of the historic waterfall in front of building, Palm Trees and Blue Skies and Great Sun Sets. 2 Pools (1 for kids), Fitness Room, , 3 lighted Tennis courts, boat marina, gazebo, ...

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Property Type

Siesta Key Condo

Featured review

"Absolutely gorgeous property"

Absolutely gorgeous property. The grounds and the property were kept beautifully. All of the amenities that were promised, were there. Being so close to the beach was a plus. There was no need to rent a ...

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Siesta Key Villa
4 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 2 bathrooms
11 reviews

$324

avg/night

$324
avg per night
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Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

NEWLY RENOVATED IN 2023!!VERY SPACIOUS 4 BEDROOM 2 BATHROOM DETACHED VILLA IN HIGHLY SOUGHT AFTER POLYNESIAN GARDENS COMMUNITY ON BAY SIDE OF THE ROAD. PUBLIC BEACH ACCESS AT CRESCENT BEACH AND ACCESS TO HEATED POOL AND COMMUNITY CENTER. WIRELESS INTERNET ACCESS,VILLA SLEEPS 8, 1 KING, 1 QUEEN, ...

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Property Type

Siesta Key Villa

Featured review

"Great Space."

This villa had great space for our family. Room for everyone. Loved having beach towels provided—Saved on suitcase space. Pool not available due to recent hurricanes. Quiet community. Good, quick ...

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Siesta Key Condo
1 BR | 1 BA | Sleeps 2 | Quick View
Sleeps 2, 1 bedroom, 1 bathroom
10 reviews

Distance to beach: 0.5 miles to Siesta Key Main Beach

$169

avg/night

$169
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Sweet Siesta Key Condo, Spacious and Quiet One Bedroom with King Bed. Walk right over to Siesta Key Main Beach. Please note that RATES ALREADY INCLUDE 13% TAXES. Condo is walking distance to Siesta Key Main Beach, entrance crops the street from this complex. And you are also a nice 0.8 mile sidewalk ...

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Property Type

Siesta Key Condo

Featured review

"Great place to stay"

Perfect location, situated right in the middle of the village and the south bridge. Restaurants and entertainment either way. It's a 2 min walk to the beach. The condo had everything I needed to make my ...

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Siesta Key Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms
3 reviews

Distance to beach: 0.1 miles to Crescent Beach on Siesta Key

$162

avg/night

$162
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • Rentals by owner
  • WiFi

About this property

This 2nd floor, completely renovated 2 bedroom, 2 full bath condo in Siesta Harbor with private beach access and overlooking its own private harbor is the perfect getaway to the #1 beach on Siesta Key in Sarasota, Florida. This unit is located near the community pool and hot tub along with guest grilling ...

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Property Type

Siesta Key Condo

Featured review

"Siesta Sand Dollar"

We had an amazing stay at Maria's place at Siesta Harbor. Everything had just been updated and was very modern and beautiful. We would highly recommend her unit and we are looking forward to going back ...

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Siesta Key Condo
2 BR | 2.5 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2.5 bathrooms

$388

avg/night

$388
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • Rentals by owner
  • WiFi

About this property

Summer Cove on Siesta Key is life at its finest. This gated community on Little Sarasota Bay offers a spacious 2 bedroom, 2 1/2 bath unit of luxury with the sophistication and conveniences of the finest resort located on the Key within minutes to the #1 beach in the US - Siesta Key Beach. The unit is ...

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Property Type

Siesta Key Condo

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Siesta Key Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms
3 reviews

$238

avg/night

$238
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Rentals by owner
  • WiFi

About this property

This tropical island get-away offers everything you desire for a magical, effortless vacation. Sunny, spacious second floor condo with easy indoor-outdoor living space including two queen bedrooms, each with an ensuite bathroom. Just steps to private, quiet powder-sand gulf beach and private fishing ...

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Property Type

Siesta Key Condo

Featured review

"Just perfect - a beautiful condo in a natural setting"

This is a lovely immaculate condo in a lush green setting. From my window i watched birds, ducks, and turtles on the lake . On the sweet private beach i saw pelicans, dolphins and egrets. It's tempting ...

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Siesta Key Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms

$233

avg/night

$233
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Oceanfront
  • Pool
  • Rentals by owner
  • WiFi

About this property

Our condominium is in the beautiful, gated complex of Gulf and Bay Club on Siesta key Beach, one of the top beaches in America! It has a very large kitchen, 2 King bedrooms and 2 bathrooms. It has been updated with a new King bed and gel mattress, updated bathrooms, new kitchen quartz counter tops and ...

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Property Type

Siesta Key Condo

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Siesta Key Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms
11 reviews

Distance to beach: 1 miles to Crescent Beach

$150

avg/night

$150
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

AFTER 2 HURRICANES E91 IS READY FOR GUESTS!! We thank God that our condo was spared! E91 is a completely renovated, First floor Condo, steps to the pool. Master bedroom has a King bed with on-suite bathroom and walk-in closet. Second bedroom has a Queen bed and twin bunk beds. Fully equipped kitchen ...

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Property Type

Siesta Key Condo

Featured review

"Great Condo"

My husband and I were very happy with this condo, it has great colors and craftsmanship in the upgrades. The condo is clean, comfortable and spacious: it also has all the necessary amenities for living ...

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Siesta Key House
3 BR | 3 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 3 bathrooms
3 reviews

$371

avg/night

$371
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Great house as is renovate december-2024 with new kitchen, toilets, furniture and everything is painted inside the house on Siesta key with pool and kanal. You can do fishing on the backside or have a jetski, boat there. Sometime you can see manates on the kanal. 3 bedroom with 3 bath and a nice heated ...

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Property Type

Siesta Key House

Featured review

"Perfect Location"

Located close to the village and within walking distance of the beach. Plenty of room for families and amenities which included bikes for all ages. The pool is heated and such a great perk!

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Siesta Key Condo
4 BR | 4.5 BA | Sleeps 10 | Quick View
Sleeps 10, 4 bedrooms, 4.5 bathrooms

Distance to beach: 0.3 miles to Siesta Beach

$583

avg/night

$583
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • Rentals by owner
  • WiFi

About this property

This 4 bedroom 4.5 bathroom condo with elevator, pool and private beach access. No need to look any further as luxury awaits! This unit can be combined with the adjoining unit for 8 bedrooms total. There is a wonderful outdoor living space with dining table and lounging area, living room, dining area, ...

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Property Type

Siesta Key Condo

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Siesta Key Condo
1 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 1 bedroom, 1 bathroom
7 reviews

$159

avg/night

$159
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Our little piece of paradise is a one bedroom condominium ideal for couples or young families. We are located at 73 Avenida Messina in unit #7 on the ground floor of the Gulf Holiday Apartments. We are 300 ft. from the Gulf of Mexico and about a five minute walk from the village - known for its shops, ...

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Property Type

Siesta Key Condo

Featured review

"Condo #6"

We enjoyed staying in Condo #6 for two nights before Hurricane Helene arrived. We evacuated and weren’t able to return. We hope to stay here again in the future. We have stayed in these condos for ...

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Siesta Key House
5 BR | 4 BA | Sleeps 13 | Quick View
Sleeps 13, 5 bedrooms, 4 bathrooms
13 reviews

Distance to beach: 400 feet to Siesta Beach

$871

avg/night

$871
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • WiFi

About this property

Excellent location at only 120 Yards To The Cool White Quartz Sand Of Siesta Beach! ?This Home Has Water Frontage on a Navigable Canal to the Bay And Then The Gulf of Mexico , Pool, Hot Tub And BBQ Area Within A Screen Enclosure. There Is A Nice Sized Sunning Patio As Well With Views Down The Waterway. ...

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Property Type

Siesta Key House

Featured review

"Amazing home!"

We had an amazing time with our family at this home in SK! David (property manager) was incredibly responsive to our questions and even stopped by to introduce himself when we arrived!The space was ...

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Siesta Key House
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms
2 reviews

Distance to beach: 400 feet to Siesta Beach

$633

avg/night

$633
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Prime location, being only two minutes walk to Siesta Beach entrance from this attractive three bedroom, two bath florida ranch! You live around the ground level pool with large patio doors openings from the two living areas and kitchen/dinning area. The home has been freshened with a very nice decor ...

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Property Type

Siesta Key House

Featured review

"Perfect Beach Getaway at Siesta Key"

Out stay at this beach vacation home was nothing short of spectacular! From the moment we arrived, we were captivated by the stunning views of the ocean. The home is just steps away from the pristine, powdery ...

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Siesta Key Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms
14 reviews

$245

avg/night

$245
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Pool
  • Rentals by owner
  • WiFi

About this property

Located on siesta Key in Sarasota, FL. The Palm Bay Club has two heated pools both Bayside and Gulfside. A private marina, dock, spa, tennis courts, fitness rooms and is located on Crescent Beach voted number one beach USA 2014Sarasota is located approximately 40 minutes South of Tampa. 1 1/2 hour ...

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Property Type

Siesta Key Condo

Featured review

"Beautiful condo, great value!"

Spacious, very clean, comfortable, and a very competitive price for what you are getting, would definitely stay here again

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Siesta Key House
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms
3 reviews

Distance to beach: 0.4 miles to Siesta Key Beach

$540

avg/night

$540
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Location, location, location!! New pool and spa just completed! Waterfall edge from spa to pool and deck jets. New landscaping with additional seating areas near pool and canal. Also, lots of green space to enjoy too!Canal home in heart of the Siesta Key Village, no need for a car! Steps away ...

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Property Type

Siesta Key House

Featured review

"Excellent"

The house was extremely clean and nothing was missing. Loved my stay from beginning to end. Melissa checked in a few times to make sure I was happy. I would stay at this home again. It has raised my bar ...

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Siesta Key Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms
2 reviews

$308

avg/night

$308
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • Private pool
  • Rentals by owner
  • WiFi

About this property

MONTHLY RENTAL. Introducing our BEAUTIFUL NEW LISTING! Nestled within this premier condominium complex, our home offers direct access to the highly acclaimed Siesta Key Beach without the need to cross any streets.Our home away from home is perfect for those seeking a winter retreat or anyone seeking ...

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Property Type

Siesta Key Condo

Featured review

"CASARINA on Siesta Key Beach-#1 Beach, Place to Visit, Hosts"

To start off with Chris and Jeannie are the best hosts to deal with. Easy going, prompt if anything is needed! They share their lovely home with us vacation lovers visiting literally the #1 Beach-Siesta ...

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Siesta Key Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms

Distance to beach: 800 feet to Siesta Key Beach

$165

avg/night

$165
avg per night
View Details

Key Amenities

  • Air conditioning
  • Oceanfront
  • Pool
  • Rentals by owner
  • WiFi

About this property

Brand New Condo, completely renovated. 2 Bedroom, 2 Bath large condo with granite kitchen and baths. Tile deck flooring. Full water views from our 6th floor location. See all the way to end of Anna Marie on clear day. Ringling bridge, downtown Sarasota, Lido and Bird Key views. King bed in master ...

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Property Type

Siesta Key Condo

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Siesta Key Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms
15 reviews

$229

avg/night

$229
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Pool
  • Rentals by owner
  • WiFi

About this property

Roomy 2 bedroom, 2 full bath condo in prime Siesta Key location. Comfortably furnished living room, dining area, all linens and fully equipped kitchen included, ceiling fans in all rooms, Flat screen tv in living room with DVD player and a flat screen in the master bedroom. Master bedroom has queen-size ...

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Property Type

Siesta Key Condo

Featured review

"Comfortable unit"

The property was nice and comfortable. The children enjoyed the pool that was close to the unit. Owner promptly responds if we had questions.

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Siesta Key Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms
3 reviews

$279

avg/night

$279
avg per night
View Details

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

Newly renovated, 4th floor condo with gulf views, a private beach, and a private fishing pier. This space was completely renovated in 2020 with all new features (including central AC) and furniture throughout. The fully-stocked kitchen is equipped with everything you need for a home-cooked meal. With ...

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Property Type

Siesta Key Condo

Featured review

"Modern Beach Condo: Hidden Gem of Siesta Key"

This modern beach condo is one of the best kept secrets of Siesta Key. While I had hoped to keep it that way, all I can offer is a ringing endorsement and review for the owners (who are incredibly kind ...

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Siesta Key Bungalow
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms
6 reviews

Distance to beach: 0.4 miles to Beach access 10 of Siesta Beach

$184

avg/night

$184
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Rentals by owner
  • WiFi

About this property

*Calendar month rentals only*May-October (3-7 month lease) - $3900 per month plus utilities and tax. November & December - $6900 per month plus utilities January, February, & March - $9800 per month plus utilities April - $7900 per month plus utilities 50% deposit upon booking, balance ...

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Property Type

Siesta Key Bungalow

Featured review

"A Great Home Away from Home"

I loved my two months at Blue Lagoon. It has a great location, near the beach and the village. Palm Island is a great neighborhood, a secluded enclave within Siesta Key. I got to know a lot of my neighbors ...

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Siesta Key Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms

$413

avg/night

$413
avg per night
View Details

Key Amenities

  • Air conditioning
  • Oceanfront
  • Private pool
  • WiFi

About this property

BREATHTAKING GULF FRONT, 2 BEDROOM / 2 BATH UNIT IN THE BEAUTFUL CRYSTAL SANDS COMPLEX. GRANITE COUTERTOPS, TILE FLOORS IN KITCHEN, BATHS and LIVING ROOM, AND WOOD FLOORING IN BEDROOMS. LEATHER FURNITURE, 3 FLAT SCREEN T.V.'S, WASHER / DRYER AND SCREENED LANAI OFF ALL ROOMS WITH DIRECT ACCESS. HIGH ...

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Property Type

Siesta Key Condo

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Siesta Key Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms
1 review

$413

avg/night

$413
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

BREATHTAKING, DIRECT OCEANFRONT, 2 BEDROOM / 2 BATH UNIT WITH PANORAMIC VIEWS OF THE BEACH AND SARASOTA SKYLINE. GRANITE COUTERTOPS, TILE FLOORS IN KITCHEN, BATHS and LIVING ROOM, AND WOOD FLOORING IN BEDROOMS. LEATHER FURNITURE, 3 FLAT SCREEN T.V.'S ( 65 LIV ROOM) I-POD DOCKING STATION, WASHER / ...

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Property Type

Siesta Key Condo

Featured review

"Great condo"

Location and condition and furnishings of condo are the best, the only suggestion we have (and it's not a deal breaker ) is a recliner or two would be great.

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Siesta Key Condo
2 BR | 2 BA | Sleeps 5 | Quick View
Sleeps 5, 2 bedrooms, 2 bathrooms
2 reviews

$220

avg/night

$220
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • Rentals by owner
  • WiFi

About this property

SIESTA KEY.GETAWAY Experience a luxury condo with a view. Located on the world renowned Crescent Beach at Siesta Key. Gulf and Bay Club is a 32 acre resort community with exceptional beach access, top notch amenities and amazing sunsets. 6 pickle ball courts. 5 hard court, 1 clay tennis courts. Gym. ...

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Property Type

Siesta Key Condo

Featured review

"Fabulous beachfront condo"

December '24 & January 2025 embraced the beauty of Siesta Key Beach at this great condo. The comforts of "home away from home" are prevalent in this well kept unit and resort. The sunsets, beach and ...

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Siesta Key Villa
3 BR | 3.5 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 3.5 bathrooms

$571

avg/night

$571
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Contemporary 3 Bedroom 3 Bath Luxury townhome. Beach views from the 3rd bedroom on top floor with full bath and bonus room and murphy bed. Master suite with tub and walkin shower, Gourmet kichen, leather furniture, balcony with partial views of the Gulf from the 3rd floor balcony. Laundry in unit, 2 car ...

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Property Type

Siesta Key Villa

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Siesta Key Condo
1 BR | 1 BA | Sleeps 3 | Quick View
Sleeps 3, 1 bedroom, 1 bathroom
2 reviews

Distance to beach: 0.0 miles to Siesta Key Main Beach

$163

avg/night

$163
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Water views everywhere from this Penthouse condo on Siesta Key! Come and enjoy beautiful weather at the best beach in Florida! Heated Pools, Lighted Tennis Courts, Fitness Gym, locker rooms, Marina, kayak launch, covered bike storage, and easy walk to SiestaKey Main Beach, and its new pickleball courts! ...

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Property Type

Siesta Key Condo

Featured review

"hurricane"

Unfortunatley we cancelled are vacation because of the back to back hurricanes Siesta Key suffered. We were very disappointed. The owner, Sue, was such a pleasure to work with. We would love to be able ...

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Siesta Key House
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms

$313

avg/night

$313
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • WiFi

About this property

Welcome to Treasure Boat Cottage, a charming beach retreat approx. 5 blocks to Siesta Key Village and the beautiful beach. This cozy home features 3 bedrooms and 2 bathrooms, offering the perfect setting for your vacation. Spend your time relaxing on one of two private outdoor patios, ideal for entertaining, ...

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Property Type

Siesta Key House

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Siesta Key Condo
2 BR | 2.5 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2.5 bathrooms

$214

avg/night

$214
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

2ND FLOOR, 2 BEDROOM / 2.5 BATH TOWNHOME LOCATED IN THE QUIET COMPLEX OF BAY OAKS. UNIT NICELY FURNISHED WITH LOTS OF SPACE. UNIT OFFERS TILE FLOORING FOR KITCHEN, DINING ROOM AND LIVING ROOM, 2 TV'S, WASHER / DRYER INSIDE UNIT, 2 SCREENED LANAI’S, SMALL BALCONY AND A FULL KITCHEN. WIRELESS ...

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Property Type

Siesta Key Condo

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Siesta Key Cottage
1 BR | 1 BA | Sleeps 2 | Quick View
Sleeps 2, 1 bedroom, 1 bathroom
4 reviews

Distance to beach: 0.5 miles to Siesta Key Beach

$139

avg/night

$139
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Rentals by owner
  • WiFi

About this property

*Calendar month rentals only*May - November (seven-month lease) - $2000 per month plus utilities May - October (three-month lease) - $2900 per month plus utilities December - $4900 per month plus utilities January, February, and March - $5900 per month plus utilities April - $4900 per month plus ...

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Property Type

Siesta Key Cottage

Featured review

"Excellent pet-friendly bungalow"

This studio was perfect for our 4 week stay in Siesta Key! The neighborhood is beautiful and quiet-and everyone we met was so friendly-to us and to our dog! Every day we walked into the Village-where ...

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Siesta Key Condo
2 BR | 2.5 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2.5 bathrooms

$551

avg/night

$551
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

THIS 3RD FLOOR CONDO WAS RECENTLY REFURNISHED WITH ALL ROOMS GETTING ALL NEW FURNITURE AND FURNISHINGS AND ALL BEDS HAVE 800 COUNT VERA WANG HOTEL- STYLE SHEETS. THIS UNIT ALSO HAS A FULLY RESTOCKED COOKS KITCHEN, GRANITE COUNTERTOPS, STAINLESS STEEL APPLIANCES, AND MUCH MORE. 2 BEDROOM / 2.5 BATH, OVERLOOKING ...

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Property Type

Siesta Key Condo

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Siesta Key Condo
1 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 1 bedroom, 1 bathroom
1 review

$202

avg/night

$202
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

This 1 bedroom , 2nd Floor unit in Siesta Village offers, great location 2 buildings from the beach, 1 block into the village with restaurants and shopping. The unit offers, central air, leather furniture, updated kitchen, 2 TV's. Complex offers community pool and laundry facilities located off common ...

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Property Type

Siesta Key Condo

Featured review

"Siesta Key paradise"

We had a great vacation here! Condo was very nice, clean and well supplied. Close to Siesta Village, Beach and within walking distance of almost everything. A definite hidden treasure!

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Siesta Key House
4 BR | 2.5 BA | Sleeps 9 | Quick View
Sleeps 9, 4 bedrooms, 2.5 bathrooms

$455

avg/night

$455
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Tucked away amid the tropical tranquility of Siesta Keys Grand Canal, this remodeled home delivers on design, location and lifestyle. Featuring four bedrooms, two-and-one-half baths and a one-car garage and washer and dryer. Beautiful hardwood floors, solid wood cabinetry and sleek granite countertops. ...

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Property Type

Siesta Key House

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Siesta Key Condo
4 BR | 2.5 BA | Sleeps 10 | Quick View
Sleeps 10, 4 bedrooms, 2.5 bathrooms

$676

avg/night

$676
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to paradise! Your oasis awaits you. 4 bedrooms, 2.5 bath luxury townhome with a private pool is just 1 block from Siesta Village and only 2 blocks from the beach! Five star amenities include; Fully stocked gourmet kitchen with granite counter tops, top of the line stainless steel appliances, laundry ...

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Property Type

Siesta Key Condo

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Siesta Key Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms

$467

avg/night

$467
avg per night
View Details

Key Amenities

  • Oceanfront
  • Pool
  • WiFi

About this property

SPECTACULAR VIEWS FROM THIS 2 BEDROOM / 2 BATH BEACHFRONT, GROUND FLOOR UNIT LOCATED IN THE CASA MAR COMPLEX WITH THE WORLD FAMOUS SIESTA KEY BEACH JUST A FEW FEET AWAY. THE CASA MAR COMPLEX OFFERS 2 POOLS, TENNIS, WIFI, (SIESTA 4- RENT DOES NOT OFFER TECH SUPPORT), COMMUNITY LAUNDRY ROOM, AND 1 COVERED ...

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Property Type

Siesta Key Condo

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Siesta Key Condo
3 BR | 2.5 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 2.5 bathrooms

$624

avg/night

$624
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

WATCH PARROTS FLY OVERHEAD FROM THIS 3 BEDROOM , 2 .5 BATH, HOME WITH POOL, FANTASTIC UNIQUE LOCATION NESTLED JUST A SHORT DISTANCE TO BOTH SIESTA KEY’S ‘VILLAGE’ AND TO THE BEACH! QUIET NEIGHBORHOOD. LARGE DECK SURROUNDS ALMOST ½ OF THE HOUSE: PARKING FOR 2 CARS IN DRIVEWAY. ...

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Property Type

Siesta Key Condo

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Siesta Key Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms

$353

avg/night

$353
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • WiFi

About this property

Welcome to Siesta Key living in this charming 2nd floor duplex in Siesta Village. This gem offers a perfect blend of comfort and convenience. Nestled in the heart of the village. this unit offers 2 bedrooms and 2 baths with a large shared pool with the unit downstairs. This quaint unit features a washer/dryer ...

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Property Type

Siesta Key Condo

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Siesta Key Condo
1 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 1 bedroom, 1 bathroom

$202

avg/night

$202
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Spectacular, modern 1 bedroom , 2nd Floor unit in Siesta Key Village offers great location 2 buildings from the beach, 1 block into the village with restaurants and shopping. The unit offers, central air, leather furniture, updated kitchen, 1 flat screen TV. Complex offers heated community pool and laundry ...

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Property Type

Siesta Key Condo

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Siesta Key Condo
5 BR | 3.5 BA | Sleeps 14 | Quick View
Sleeps 14, 5 bedrooms, 3.5 bathrooms

$802

avg/night

$802
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

This 3600 sq ft., 5 Bedroom 3.5 Bath, Townhome Offers, Private heated pool, ** Please be aware that the pool is refreshing, but has limited space for larger parties. many balconies overlooking the pool. Beautiful custom kitchen, with Granite and Stainless. LAYOUT of the HOUSE : Ground floor off the pool ...

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Property Type

Siesta Key Condo

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Siesta Key Condo
2 BR | 1.5 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 1.5 bathrooms

$224

avg/night

$224
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

COME RELAX IN THIS 3RD FLOOR, FIRETHORN UNIT LOCATED IN MIDNIGHT COVE I, BAYSIDE. COMPLEX OFFERS 2 POOLS, BEACH CHAIRS PROVIDED BY ASSOCIATION, 2 TENNIS COURTS AND BEACH ACCESS THROUGH THE GULF SIDE. (NO BEACH CHAIRS OR EQUIPMENT PROVIDED) 3RD FLOOR UNIT, (NO ELEVATOR) HAS OPEN BALCONY WITH VIEW OF CANAL, ...

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Property Type

Siesta Key Condo

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Siesta Key Condo
2 BR | 1.5 BA | Sleeps 5 | Quick View
Sleeps 5, 2 bedrooms, 1.5 bathrooms

Distance to beach: 250 feet to Siesta Key

$172

avg/night

$172
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

On Siesta Key - Quick walk to Siesta Key's world famous beach. Beautiful and private, this updated condo with granite kitchen and tile floors overlooks the bay inlet and boat basin. Across street from world famous beach. Fully amenitied condo in amentied condo complex. Large community pool, tennis ...

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Property Type

Siesta Key Condo

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Siesta Key Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms
1 review

$467

avg/night

$467
avg per night
View Details

Key Amenities

  • Pool
  • WiFi

About this property

BREATHTAKING VIEWS FROM THIS 2 BEDROOM / 2 BATH BEACHFRONT, GROUND FLOOR UNIT LOCATED IN THE CASA MAR COMPLEX WITH THE WORLD FAMOUS SIESTA KEY BEACH JUST A FEW FEET AWAY. THE CASA MAR COMPLEX OFFERS 2 POOLS, TENNIS, WIFI, (SIESTA 4- RENT DOES NOT OFFER TECH SUPPORT), COMMUNITY LAUNDRY ROOM, AND 1 COVERED ...

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Property Type

Siesta Key Condo

Featured review

"Casa Mar # 40"

We rented Casa Mar # 40 for two weeks. We have stayed in this unit in the past and highly recommend it. The condo was very comfortable, clean and well supplied. The location is incredible! Siesta Key Beach ...

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Siesta Key Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms

$210

avg/night

$210
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

2ND FLOOR UNIT, COMPLEX OFFERS, POOL, WIFI AT THE POOL AREA ONLY. ( SIESTA 4 RENT DOES NOT OFFER TECH SUPPORT), NEAR SHOPPING, 2 BLOCKS TO THE PUBLIC BEACH ACCESS, END UNIT OFFERS A LITTLE MORE SPACE. 2 WEEK MIN. LAUNDRY FACILITY ON 1ST FLOOR. 1 King, 2Twin, 1SOFA BED. CLEANING FEE $205

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Property Type

Siesta Key Condo

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Siesta Key Vacation Rentals

Monthly Rentals in Siesta Key

Your Ideal Monthly Rental Awaits

Explore a range of monthly rentals in Siesta Key, from beachfront condos to luxurious homes with ocean views. Whether you want to be close to Siesta Beach or prefer a quiet retreat near Crescent Beach, there’s a rental to suit your needs. Enjoy the comfort of a long-term stay in this coastal paradise.

Why Rent Monthly?

  • Cost-Effective: Monthly rentals offer lower rates compared to shorter stays, making them perfect for long-term vacations or work trips.
  • Home-Like Comfort: Fully furnished rentals provide kitchens, spacious living areas, and private bedrooms for the ultimate comfort during your extended stay.
  • Relax and Settle In: Unpack, unwind, and explore Siesta Key without the rush, making the most of your time in this beautiful location.
  • Live Like a Local: A longer stay allows you to experience Siesta Key’s unique charm, from its powdery white sands to its lively village scene.

Book Your Monthly Rental Today

Don’t wait to secure your ideal long-term rental in Siesta Key. Browse our listings and find the perfect property for your extended stay. Whether you’re looking to escape the cold or enjoy a warm, sunny vacation, Siesta Key is the place to be.

Plan Ahead for Future Stays

Booking in advance is the best way to ensure you get the rental you want, especially during the busy winter months when Siesta Key is in high demand.

Amenities and Perks for Long-Term Stays

  • Fully Furnished Rentals: Enjoy move-in-ready homes complete with fully equipped kitchens and comfortable living spaces.
  • Flexible Dates: Choose your move-in and move-out dates with ease, perfect for extended stays.
  • Transparent Monthly Pricing: Enjoy competitive rates with no hidden fees.
  • Remote Work Ready: Many rentals offer high-speed Wi-Fi and dedicated workspaces, ideal for remote workers.

Popular Amenities for Monthly Rentals

  • 🥘 Full kitchen
  • 📶 High-speed Wi-Fi
  • 🐾 Pet-friendly options
  • 💻 Workspace for remote professionals
  • 🚗 Free parking

Monthly Rentals in Siesta Key for Every Traveler

Group-Friendly Rentals

Planning a group vacation or family reunion? Siesta Key offers spacious rentals with multiple bedrooms and large living spaces, perfect for groups looking to enjoy a relaxed beach getaway.

Family-Friendly Monthly Rentals

Siesta Key is ideal for families with attractions like Siesta Beach, Point of Rocks, and Turtle Beach. Our family-friendly rentals provide ample space, outdoor areas, and proximity to kid-friendly activities like boating, snorkeling, and wildlife viewing.

Romantic Getaways for Couples

Siesta Key’s romantic sunsets and tranquil beaches make it a great destination for couples. Enjoy cozy monthly rentals with ocean views, private pools, and easy access to intimate dining and beachside strolls.

Winter Retreats for Snowbirds

Siesta Key is a favorite among snowbirds seeking to escape the cold northern winters. With its warm weather, stunning beaches, and a laid-back atmosphere, it’s no wonder snowbirds flock here each winter. Our monthly rentals provide a comfortable and convenient home base for an extended stay.

Why Siesta Key is Perfect for Snowbirds

  • Mild Winter Climate: Enjoy average winter temperatures in the 70s, making Siesta Key an ideal escape from the cold.
  • World-Class Beaches: Siesta Beach is consistently ranked among the best beaches in the world, offering powdery white sand and clear waters.
  • Active Lifestyle: Stay active with a variety of outdoor activities, including beach walks, biking, and water sports.
  • Community and Convenience: Siesta Key offers a welcoming community atmosphere with easy access to everything you need, from grocery stores to healthcare services.

Book Your Winter Stay Now

Don’t miss out on your chance to spend the winter in paradise! Reserve your long-term rental in Siesta Key today and enjoy everything this beautiful destination has to offer.

Outdoor Activities in Siesta Key

Siesta Key is known for its stunning beaches and outdoor adventures. Staying in one of our monthly rentals puts you close to:

  • Beaches: Relax on Siesta Beach, Crescent Beach, or Turtle Beach for sunbathing, swimming, and beachcombing.
  • Water Sports: Try kayaking, paddleboarding, or parasailing, with equipment rentals and tours available at the beach.
  • Fishing: Whether you’re casting from the shore or taking a fishing charter, Siesta Key offers excellent opportunities for anglers.
  • Nature and Wildlife: Explore local parks and nature reserves, such as the nearby Myakka River State Park, for hiking, birdwatching, and wildlife viewing.

Seasonal Information about Siesta Key Monthly Rentals

💰 Highest rates
December through March

🎉 Busiest month
February

🏠 Popular home types
Beachfront condos and single-family homes

🔥 Hottest months
July and August

❄️ Coldest months
January and December

Rainiest months
June through September

🌺 Best months for flowers
April and May

🌴 Peak tourist season
December through March

🍂 Quietest months
September and October

🌊 Best beach months
March through May

🏌️ Best golfing months
November through April

🎨 Top cultural events
Siesta Key Crystal Classic Sand Sculpting Festival (November), Siesta Fiesta Art Festival (April)

🍽️ Best dining months
January through March

🦋 Best months for nature activities
March through May

🛶 Best water sports season
June through September

🏖️ Best months for shelling
May and June

📅 Local festivals peak
November through April