Siesta Key Rentals by Owner

(71 rentals)
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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
View Details

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
78 reviews

Distance to beach: 0.0 feet to We are directly on the beach and direct oceanfront

$344

avg/night

$344
avg per night
View Details

Key Amenities

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

About this property

Our condo is directly on the beach and is direct oceanfront (Gulf-front). Unfortunately, there are properties on this site that falsely claim to be beachfront / oceanfront. We encourage travelers to ask property owners to verify those claims.When we travel over 1,000 miles to enjoy a beach vacation ...

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Property Type

Siesta Key Condo

Featured review

"PERFECT BEACH CONDO"

This condo was amazing! The hosts were very polite and responsive. The condo was clean and well-equipped with everything we needed, including a beach wagon, chairs, sand toys, umbrellas, a boogie board, ...

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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 House
4 BR | 2.5 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 2.5 bathrooms
9 reviews

$800

avg/night

$800
avg per night
View Details

Key Amenities

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

About this property

Hurricane Update: We lucked out! Hurricane Helene did not flood our beach house except for the carport. We need to replace the hot water heater, the washer and dryer, and some walls and doors made of wood. Hurricane Milton damaged some soffits but they have already been repaired.A front row seat ...

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Property Type

Siesta Key House

Featured review

"Perfect location! Wonderful accommodations!"

Booked this spot for the first time and spent a wonderful week there with my three sisters for a birthday celebration. The weather was great and the beach and water were everything we had hoped it would ...

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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
View Details

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 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms
7 reviews

$435

avg/night

$435
avg per night
View Details

Key Amenities

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

About this property

THE BEACH IS CALLING AND I MUST GO!! *We invite you to come stay with us in the Crescent Arms South Tower--Condo 601S--directly on the #1 famous Crescent Beach with a FULL view of the Gulf on a private 32 foot lanai.*Decorated in a "beachy motif" with granite counter tips in the kitchen ...

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Property Type

Siesta Key Condo

Featured review

"Loved our stay!"

Property was as described and exactly what we were looking for as a base for our week on Siesta Key and surrounding area! Beautiful condo, beach was perfect, and location was ideal for activities and restaurants. ...

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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 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms
2 reviews

$316

avg/night

$316
avg per night
View Details

Key Amenities

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

About this property

Condo, 2 Bedrooms, 2 Baths, Sleep Sofa (Sleeps 4-6)If you are looking for a terrific vacation spot tastefully decorated, clean, and comfortable, you just found it. You can be as lazy as the sun and free as the Gulf breeze. This is the ‘Best Location’ on ‘Crescent Beach.’ Experience ...

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Property Type

Siesta Key Condo

Featured review

"Wonderfully Relaxing"

Staff, wonderful, front desk also wonderful. Snythyou need is a call away. Condo comfortable and clean

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

$344

avg/night

$344
avg per night
View Details

Key Amenities

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

About this property

A millionaire's retreat! This completely remodeled first floor unit with view of the Gulf of Mexico and amazing sunsets awaits you on Siesta Key. Walk out the lanai door directly to the beach where children can play within view or walk over the boardwalk to the blue-green waters of the Gulf within ...

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Property Type

Siesta Key Condo

Featured review

"You WILL NOT be disappointed with this condo!!!"

I have nothing but rave reviews of this rental - the location, the condo itself and the owners. We had an amazing time and they had anything and everything that you could want in the condo. We will definitely ...

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

$233

avg/night

$233
avg per night
View Details

Key Amenities

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

About this property

You will fall in love with this condo! Everything you would possibly need is provided. Enjoy relaxing on the lanai in the morning with your coffee or a glass of wine in the evening. Nice beach chairs, beach umbrellas, straw mats, small cooler, swim noodles and a beach bag are all in the condo for your ...

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Property Type

Siesta Key Condo

Featured review

"Just what we wanted."

Just returned from a week in Karen’s condo. Her place is perfect. The balcony and view were wonderful. Sitting and looking at the beach was so relaxing. The condo was great. Gave you a beach feeling. ...

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Siesta Key Condo
3 BR | 2 BA | Sleeps 10 | Quick View
Sleeps 10, 3 bedrooms, 2 bathrooms
14 reviews

Inquire for rates

Inquire for rates

View Details

Key Amenities

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

About this property

Known for its quartz sand and crystal clear waters, the beaches of Siesta Keys are ranked No. 2 in the U.S. and No. 9 globally as one of the best travel destinations in 2024. Siesta Key, a barrier island in the Gulf of Mexico, is less than a 30 min drive from SRQ Airport. This vacation rental is one of ...

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Property Type

Siesta Key Condo

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

$344

avg/night

$344
avg per night
View Details

Key Amenities

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

About this property

This beautiful, completely remodeled 2-bedroom, 2-bathroom condo offers the perfect getaway on Siesta Key’s southern end, directly facing the Gulf of Mexico. With brand-new tiled floors, a modern kitchen featuring granite counters, stainless steel appliances, and a fully equipped bar area, this ...

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Property Type

Siesta Key Apartment

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Siesta Key Condo
2 BR | 1.5 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 1.5 bathrooms
32 reviews

Distance to beach: 200 yards to Crescent Siesta Key Beach

$231

avg/night

$231
avg per night
View Details

Key Amenities

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

About this property

Located in beautiful Siesta Key, Fl (consistently ranked #1 beach in the US!!) in Midnight Cove 1, this bayside condo spoils its occupant with all the amenities and luxuries needed for a relaxing, tropical vacation. Nestled amid lush landscaping in this gated community, our unit is newly remodeled and ...

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Property Type

Siesta Key Condo

Featured review

"New Year Getaway"

We loved Sandy's condo. It was stocked with everything you will need . This was the cleanest rental we have ever stayed in. We only got in our car to drive one time the whole week- could walk to everything ...

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

$344

avg/night

$344
avg per night
View Details

Key Amenities

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

About this property

This magnificent unit has been completely remodeled and is on the ground floor with beautiful water views and spectacular sunsets. Walk out the rear lanai door directly onto the beach where children can play within view or walk over the boardwalk to the blue-green waters of the Gulf of Mexico within 100 ...

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Property Type

Siesta Key Condo

Featured review

"Little piece of heaven"

I can't say enough about this property absolutely heaven out your front door is a beautiful Bay with manatees playing in it pretty much every day we were able to be there!! out the back door you're about ...

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

$413

avg/night

$413
avg per night
View Details

Key Amenities

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

About this property

Stunning Oceanfront Condo on Siesta KeyStep into your private paradise! This condo offers breathtaking ocean views from the living room, master bedroom, kitchen, and lanai. Imagine waking up to the sound of waves and ending your day with the sun dipping into the Gulf—this is coastal living at ...

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Property Type

Siesta Key Condo

Featured review

"Turtle Beach"

I had not realized the condo I picked was not in Siesta Keys, but that is my fault. The condo was very clean on a private beach in Turtle Beach. Very spacious and newly renovated. Everything we needed

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

$301

avg/night

$301
avg per night
View Details

Key Amenities

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

About this property

This magnificent unit is on the third floor with spectacular unobstructed views of the Gulf! This unit has been completely renovated with beautiful natural stone tile throughout, updated kitchen and bathroom and brand new furniture, coastal pictures, decorative accessories, bedding, new paint throughout. ...

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Property Type

Siesta Key Condo

Featured review

"Just Perfect"

Location was amazing - views spectacular, nothing separating us from the beautiful gulf. Condo - was missing nothing and needed nothing additional. Clean. Stocked. Convenient. Comfortable. Owners - ...

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

$409

avg/night

$409
avg per night
View Details

Key Amenities

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

About this property

Very private - empty lot across the canal and fenced in. Walk to the islands best restaurants, bars, shops and ice cream parlors. The beach is a short stroll (8 min), use free golf cart taxi or ride provided bikes with tow behind cart! Siesta is well known for its #1 beach in the USA!

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Property Type

Siesta Key House

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

$323

avg/night

$323
avg per night
View Details

Key Amenities

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

About this property

Our Condo is on beautiful Turtle Beach at the southern and most private end of Siesta Key directly on the Gulf of Mexico. When we say directly, we mean directly and not merely a Gulf “View” or a long car ride or a long walk to the Gulf. We call it “Paradise” and you could not ...

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Property Type

Siesta Key Condo

Featured review

"Excellent Condo A306"

We stayed at A306 the third week of April 2023. Our stay was well beyond expectation and this location & Unit is the best overall rental we’ve experienced in 25+ years of Florida vacationing. Everything ...

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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 Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms
11 reviews

Distance to beach: 0.2 miles to Siesta Key Beach

$265

avg/night

$265
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Our adorable unit – Casita Siesta - is located at Gulf & Bay Bayside on Siesta Key, on the bay just south of Sarasota and with private beach access to world-famous Siesta Key Beach. It is a lovely 2 bdr/2 bath unit with a spacious living room and sunny lanai. The master bedroom has full bathroom ...

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Property Type

Siesta Key Condo

Featured review

"Mullins review"

The place was very clean. The location was perfect for beach trips and trolleys for visiting the village.

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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 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms
9 reviews

$305

avg/night

$305
avg per night
View Details

Key Amenities

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

About this property

If you are looking for a terrific vacation spot tastefully decorated, clean, and comfortable, you just found it. You can be as lazy as the sun and free as the Gulf breeze. We are not underselling ourselves when we say we have the 'Best Location' on 'Crescent Beach.' Experience the ...

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Property Type

Siesta Key Condo

Featured review

"Beware of Horrible Communication"

My husband and I intended to stay here in early February. On several occasions we reached out to customer service regarding damage from the hurricane. A letter was sent that only said “some amenities ...

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

$342

avg/night

$342
avg per night
View Details

Key Amenities

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

About this property

RENOVATED 2020!!! From the lanai and your private patio, you are directly on the beach where it is easy to keep an eye on the children playing, or walk down to the Gulf of Mexico for a swim. Located on Turtle Beach, Siesta Key's quiet south end - this lovely Gulf front first floor unit with large ...

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Property Type

Siesta Key Condo

Featured review

"Beautiful Condo!"

This Condo is well appointed and is in the perfect spot right on the beach of the Gulf! We we're ableto walk out to the beach from our back door and see the canal out the front. We cooked in the kitchen ...

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

$421

avg/night

$421
avg per night
View Details

Key Amenities

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

About this property

Crystal Sands, Siesta Key, SarasotaAmazing Views!! Our property is right on the beach. Take the elevator down and you're at the ocean. The views are amazing as you can see in the pics. Sit on the lanai for breakfast and watch the activities on the beach, or have a glass of wine and watch ...

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Property Type

Siesta Key Condo

Featured review

"AMAZING 2-Weeks!!!!!"

We loved every minute of our 2-week stay at Crystal Sands, the unit was beautiful and views breathtaking. We were a stones throw from the beach and it couldn't have been any better. I highly recommend!

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

$280

avg/night

$280
avg per night
View Details

Key Amenities

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

About this property

This updated Villa is on the beach side of Siesta Key, with private beach!!!Newly renovated private villa! Beautiful brand new kitchen with quartz countertops and stainless steel appliances. All new flooring through out and newly decorated!Be one of the first guests in this newly renovated clean ...

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Property Type

Siesta Key Villa

Featured review

"Highly Recommend!"

I would highly recommend renting through Ruth. Her villa was in the perfect location, with great beach access and it was newly renovated! Ruth was easily accessible and answered every question I had. The ...

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

$227

avg/night

$227
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Located in beautiful Siesta Key, Fl. this bayside condo is full of amenities needed for a relaxing beach vacation. Two tennis courts with Pickleball available, two heated pools, covered private parking, outdoor gas grills, boat docks, outdoor bathrooms within this private, gated community.Walk to ...

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Property Type

Siesta Key Condo

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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 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms
5 reviews

$275

avg/night

$275
avg per night
View Details

Key Amenities

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

About this property

Beautiful 2 Bedroom, 2 Full bath condo. Close to everything, right on Crescent Beach, voted #1 beach twice in the last 5 years. King in the master, 2 full size beds in the second.

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Property Type

Siesta Key Condo

Featured review

"Jamaica Royal"

We loved our stay here. Right on the beach and great pool close to our condo. Clean and spacious. Maybe could use a few updates but we were mainly here at night for sleeping so it worked well for us.

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

$322

avg/night

$322
avg per night
View Details

Key Amenities

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

About this property

This 5th floor two bedroom, two bath condo is totally and completely renovated. Be one of the first guests to stay in this beautifully renovated condo. New tile throughout. There are two bedroom suites with private baths. Each bedroom has new slider doors that open to screened in lanai with beautiful ...

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Property Type

Siesta Key Condo

Featured review

"Relaxing getaway"

We had a really nice week in this condo just steps to the beach. The powdery white sand never gets hot.The condo has all of the essentials and more. Very comfortable. And there’s a nice pool if want to ...

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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 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 Estate
6 BR | 5 BA | Sleeps 20 | Quick View
Sleeps 20, 6 bedrooms, 5 bathrooms
1 review

Distance to beach: 4 miles to Siesta Key Beach

$803

avg/night

$803
avg per night
View Details

Key Amenities

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

About this property

Create memories with friends and family at this unique, and spacious property only 10 minutes from Siesta Key Beach. It is perfect for large groups or reunions as this house includes separate living spaces and has a total of 13 beds. Right behind the main house, you will find a fun area to relax, play ...

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Property Type

Siesta Key Estate

Featured review

"A perfect vacation!"

This is a wonderful 5 plus star accommodation! The location is perfect, so convenient to the beach and so many things to do. The house is stocked with everything you need and more. Michael is an excellent ...

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

Distance to beach: 100 yards to Crescent Beach

$248

avg/night

$248
avg per night
View Details

Key Amenities

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

About this property

Simply relaxing one bedroom condo with a king bed facing the pool area and just a few steps to the private entrance to" Siesta Key #1 beach" white quartz sand beach . Additionally a Lazyboy queen memory foam sofa sleeper for separate sleeping area if needed Unit includes a full kitchen for ...

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Property Type

Siesta Key Condo

Featured review

"Sea Crest #26"

Great people. Great weather. Great beach access, loved the sunsets. TV had no directions on how to navigate. Loved being close to Captain Curt’s restaurant. Loved the Old Florida charm.

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

Distance to beach: 0.1 miles to Siesta Key

$800

avg/night

$800
avg per night
View Details

Key Amenities

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

About this property

Fully renovated penthouse unit! This property seamlessly melds state of the art amenities with casual beachfront living with privacy. Step off of the sugary sands of Siesta Key Beach and right in to this beautifully renovated beachfront condominium with surprisingly expansive gulf views. Sea and sky ...

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Property Type

Siesta Key Condo

Featured review

"Heaven"

I think this is what Heaven must be like.. Our stay here was wonderful! This is a beautifully renovated, clean, and comfortable unit. It is the whole top floor of a two unit building (no elevator; 27 steps ...

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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 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
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
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 Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms
11 reviews

Distance to beach: 200 feet to across street

$262

avg/night

$262
avg per night
View Details

Key Amenities

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

About this property

2 bedroom gorgeous condo overlooking Siesta Key Beach and Gulf of Mexico. Complex with large community pool, sauna, covered parking, secure gated area. Gas grills, party room, beautiful property. 2 full bathrooms with granite walk in showers and basin, etc. King bed in master with ensuite full bath, ...

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Property Type

Siesta Key Condo

Featured review

"Beautiful Property with Perfect View"

This property and the entire complex was perfect for our stay on Siesta Key. It was clean and well stocked with everything we needed. We would definitely stay again.

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

Distance to beach: 200 feet to Siesta Key Public Beach

$307

avg/night

$307
avg per night
View Details

Key Amenities

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

About this property

Single family home with private heated caged pool. Large open floor plan in living area to kitchen and enclosed pool and deck. 3 bedrooms, 2 of which are master suites with ensuite full baths, flat screen TV's, king beds, and sliding glass doors to either caged pool deck or open air sundeck. 3rd ...

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Property Type

Siesta Key House

Featured review

"Siesta Beach"

Absolutely the best location! House was clean and has everything you need. Especially liked pulling wagon with all the beach items the short distance to the beach. Owners very helpful and quickly replaced ...

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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 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 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 Vacation Rentals