Siesta Key Rentals by Owner

(79 rentals)
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Siesta Key Condo | On the beach
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms
14 reviews

$280

avg/night

$280
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

$550

avg/night

$550
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
1 BR | 1 BA | Sleeps 2 | Quick View
Sleeps 2, 1 bedroom, 1 bathroom
9 reviews

$251

avg/night

$251
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

You have access to a deeded walkway from your condo to the beach while living directly on the intercoastal waterway with a great view. The intercoastal waterway, with its parade of all types of boats and dolphins swimming by, is visible from practically every room. This 2nd floor, 1 Bedroom/1 Bath ...

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Property Type

Siesta Key Condo

Featured review

"Wonderful!"

This condo is perfect. Comfortable lanai with an excellent view of the intercoastal. Well appointed home (Best one we have ever stayed in). Everything in the condo was organzied and easy to find. Walk ...

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

Distance to beach: 250 feet to Crescent Beach

$422

avg/night

$422
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Direct-with-Owner Rentals: Siesta Breakers #603 offers "All-In Price" 15% to 30% Discounted Rental Rates from $1,958 to $3,708 /Wk Depending on the Season ($150 departure cleaning extra - $400.00 refundable security deposit required) & SAVINGS from $420 to $913 /Wk from the listed Siesta ...

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Property Type

Siesta Key Condo

Featured review

"Lovely"

The condo was very clean and comfortable. Beautiful view from the lanai. Great location, walking distance to many restaurants and ice cream parlors!

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Siesta Key Estate
6 BR | 5 BA | Sleeps 20 | Quick View
Sleeps 20, 6 bedrooms, 5 bathrooms

Distance to beach: 4 miles to Siesta Key Beach

$833

avg/night

$833
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

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

$185

avg/night

$185
avg per night
View Details

Key Amenities

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

About this property

This two bedroom(master King bed), second bedroom double bed/ single bed (with pull out trundle) full kitchen, dining, living room and lanai open into living space. Out back you sit on the bay and across the street is number 1 beach in the U.S. Pool heated year round 80 degrees, grill areas and laundry ...

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Property Type

Siesta Key Condo

Featured review

"Very nice host and home. Home needs work."

The owner could not have been nicer. The home is beautiful but does need attention to details like, no ice from icemaker, hot water takes forever to get to kitchen and master bath. Carpet in bedroom needed ...

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Siesta Key House | On the beach
3 BR | 3 BA | Sleeps 7 | Quick View
Sleeps 7, 3 bedrooms, 3 bathrooms
7 reviews

Distance to beach: 300 feet to Siesta Beach

$775

avg/night

$775
avg per night
View Details

Key Amenities

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

About this property

This home has private Siesta Key beach frontage on the prime section of beach, there are no streets to cross or homes between you and the beach. Nearly every room has a full view of the beach and Gulf of Mexico. The entire back of this house opens with stacking glass sliding doors to catch the Gulf breezes ...

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Property Type

Siesta Key House

Featured review

"Great property on the sand."

We had a great week despite the heat of summer. This house although dated was clean, cool and comfortable. It was a two minute walk through the back yard to the sand. We had a few minor house keeping ...

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Siesta Key House
3 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 2 bathrooms
1 review

$442

avg/night

$442
avg per night
View Details

Key Amenities

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

About this property

Comfortable private 3bedroom 2 bath home, open concept floor plan. The hone has a salt water heated pool. You can bike ride or walk to the main siesta key beach pavilion. There you can play pickleball or enjoy the service at the snack bar or continue out to the white quartz sand and clear waters of the ...

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Property Type

Siesta Key House

Featured review

"Definitely more than 5 stars for this property"

I’ve rented several Siesta Key properties, but this is definitely my favorite. The home is located very close to the public beach down a quiet cul de sac. The neighbors were all friendly and the area ...

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

$283

avg/night

$283
avg per night
View Details

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

Home away from home.... I enjoy my coffee and cocktails at waterfront lanai and when I travel, I would love someone to enjoy it as well. I live in this condo, therefore, this unit has everything you may need and more. Boating, fishing, paddle boarding, kayaking, biking to Siesta Key Beach or free trolley ...

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Property Type

Siesta Key Condo

Featured review

"Spectacular"

We’ve been vacationing in Sarasota/Turtle Beach for over 10 years. This condo is our ABSOLUTE FAVORITE! Very nicely decorated & accommodating. We love that it is located on the bay. It is GREAT for fishing ...

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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
  • Hot tub
  • 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 House
3 BR | 2 BA | Sleeps 10 | Quick View
Sleeps 10, 3 bedrooms, 2 bathrooms

Distance to beach: 0.7 miles to Siesta Key Beach

$499

avg/night

$499
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • 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, hot tub, fire pit, and ...

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Property Type

Siesta Key House

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Siesta Key Studio
Studio | 1 BA | Sleeps 2 | Quick View
Sleeps 2, 0 bedrooms, 1 bathroom
5 reviews

Distance to beach: 0.3 miles to Siesta Key Beach access 10

$200

avg/night

$200
avg per night
View Details

Key Amenities

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

About this property

*Calendar month rentals only*******SPECIAL - March and April 2024 - $200 per night plus utilities - 14 night minimum****May - November (seven-month lease) - $1750 per month plus utilities May - November (three-month lease) - $2500 per month plus utilities December - $3900 per month plus utilities January, ...

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Property Type

Siesta Key Studio

Featured review

"Perfect peaceful pet friendly bungalow"

I recently had the pleasure of staying for three months in this cozy bungalow on Palm Island in the heart of Siesta Key. Nestled amidst lush vegetation and just a short walk from the beach and Siesta Key ...

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

$378

avg/night

$378
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Relax and unwind in our spacious, sun-filled villa that is situated in an idyllic private neighborhood. Enjoy quiet surroundings, perfectly situated within steps to all that Siesta Key has to offer. The open-concept villa boasts an incredible recently renovated chef’s kitchen equipped with high-end ...

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Property Type

Siesta Key Villa

Featured review

"Fantastic"

We had a wonderful week staying at this place. Definitely as advertised. Spacious, well-equipped and very clean. You can certainly travel light when you stay here. The neighborhood is quiet with a secluded ...

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

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

$282

avg/night

$282
avg per night
View Details

Key Amenities

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

About this property

*Calendar month rentals only*May-October (six-month lease) - $3500 per month plus utilities November & December - $6900 per month plus utilities January, February, & March - $8900 per month plus utilities April - $7900 per month plus utilities 50% deposit upon booking, balance 90 prior ...

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

$329

avg/night

$329
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Be prepared to relax as soon as you walk into our completely remodeled, bright open concept, 2BR, 2BA ground floor condo. Just a five minute walk to the beach. In addition to a king and two twin beds, there is a very comfortable pull out queen bed that doubles as a luxurious leather couch. The living ...

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Property Type

Siesta Key Condo

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

Distance to beach: 0.5 miles to Siesta Beach access 7

$300

avg/night

$300
avg per night
View Details

Key Amenities

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

About this property

*Calendar month rentals only*May-October (six-month lease) - $3500 per month plus utilities November & December - $6900 per month plus utilities January, February, & March - $8900 per month plus utilities April - $7900 per month plus utilities50% deposit upon booking, balance 90 prior ...

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Property Type

Siesta Key Bungalow

Featured review

"My stay at the Canal Place in Siesta Bungalows"

I am thoroughly enjoying my stay at Siesta Bungalows!!! My place is clean, quiet, and in a fabulous location!! I am about a 5 minute walk to the village and only a 7 min walk from the breathtaking Siesta ...

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

Distance to beach: 0.5 miles to Siesta Key Main Beach

$180

avg/night

$180
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 House
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms
2 reviews

$295

avg/night

$295
avg per night
View Details

Key Amenities

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

About this property

Beautiful house on Siesta Key with private pool and generous space. 15 min walk to the beach! This charming 3-bedroom, 2-bathroom private home is located in discreet residential neighborhood, on the beautiful Siesta Key island. It offers a large fenced outdoor area, with a private pool, plenty of parking ...

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Property Type

Siesta Key House

Featured review

"great location to the Village and beach"

A wonderful location on Siesta Key--we loved being able to walk to the Village and easily walk to the beach. The house has an open feeling with a large living/eating/kitchen area. I cooked a good bit ...

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Siesta Key Apartment
2 BR | 1.5 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 1.5 bathrooms
6 reviews

$210

avg/night

$210
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Vacation rental close to the # 1 beach in the USA - Siesta Key on the Gulf of Mexico (Sarasota)Siesta Key, awarded for its pristine, powdery white beaches and its azur blue waters is the perfect escape from everyday life.*** It seems like a miracle that Midnight Cove II again was extremely ...

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Property Type

Siesta Key Apartment

Featured review

"Perfect"

We spent 18 days at the unit. The Unit is beautiful and clean. We enjoyed the location and hope to return next year.

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Siesta Key Condo | On the beach
2 BR | 2 BA | Sleeps 5 | Quick View
Sleeps 5, 2 bedrooms, 2 bathrooms
1 review

$277

avg/night

$277
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

"Perfect Stay for Relaxation and Fun!"

Our family had the pleasure of staying at this Gulf and Bay rental on more than one occasion. The condo is a hidden gem with a spectacular view, and just steps away from the beach. We could not have asked ...

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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

$241

avg/night

$241
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 2 Queen beds. Please note that RATES ALREADY INCLUDE 13% TAXES. Condo is walking distance to Siesta Key Main Beach, and a nice 0.9 mile sidewalk walk (or bike or free trolley) to Siesta Key Village. Six new Pickleball courts and 2 Tennis Courts ...

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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 | 1.5 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 1.5 bathrooms
2 reviews

Distance to beach: 950 feet to Crescent Beach

$270

avg/night

$270
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Direct-with-Owner Rental Discounts: Midnight Cove #714 offers "All-In Price" 10% to 25% Discounted Rental Rates from $946 to $2,488 /Wk Depending on the Season ($150 departure cleaning extra - $400.00 refundable security deposit required) & SAVINGS from $163 to $621 /Wk from the listed ...

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Property Type

Siesta Key Condo

Featured review

"Siesta Key Midnight Cove 714, Convienient, 1st Floor Condo, Great Complex"

Midnight Cove has all the amenities for a great getaway on Siesta Key. The complex has great beach access, beach chairs with attendant on the beach, nice pool ,fitness center and two BBQ grill areas. The ...

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Siesta Key Condo
Studio | 1 BA | Sleeps 2 | Quick View
Sleeps 2, 0 bedrooms, 1 bathroom
2 reviews

Distance to beach: 0.0 miles to Siesta Key Main Beach

$217

avg/night

$217
avg per night
View Details

Key Amenities

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

About this property

PENTHOUSE WATER VIEWS! RESORT LIVING ON SIESTA KEY at Harbor Towers Yacht & Racquet Club, gives you the best of both worlds - Beach and Resort! PENTHOUSE CONDO WITH WATER VIEWS: Spacious 1 bedroom Condo with 2 Queen beds - one queen bed in spacious Bedroom, and second Queen Bed is a brand new ...

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

Distance to beach: 850 feet to Crescent Beach

$270

avg/night

$270
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Direct-with-Owner Rental Discounts: Midnight Cove #532 offers "All-In Price" 10% to 25% Discounted Rental Rates from $946 to $2,488 /Wk Depending on the Season ($150 departure cleaning extra - $400.00 refundable security deposit required) & SAVINGS from $163 to $621 /Wk from the listed ...

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Property Type

Siesta Key Condo

Featured review

"Great stay in siesta keys"

This 2 bedroom ground floor condo was comfortable, clean, stylish and centrally located. It was fully stocked eith cleaning and cooking supplies as well as hairdryer and iron. We had a great time and ...

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Siesta Key Bungalow
2 BR | 1.5 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 1.5 bathrooms
3 reviews

Distance to beach: 0.3 miles to Siesta Key Beach

$288

avg/night

$288
avg per night
View Details

Key Amenities

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

About this property

*Calendar month rentals only*July- December (six-month lease) - $3900 per month plus utilities July- October (four-month lease) - $3500 per month plus utilities December - $6900 per month plus utilities January, February, and March- $8900 per month plus utilities April- $7900 per month plus utilities May ...

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Property Type

Siesta Key Bungalow

Featured review

"Perfect location to enjoy Siesta Key – wonderful hosts – stay here!"

Choose this home for its fantastic location, hosts and amenities - easy walk to the beach or downtown Siesta Key, but feels miles away from the crowds in its tropical setting.The home was perfect for ...

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Siesta Key Studio
Studio | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 0 bedrooms, 1 bathroom
3 reviews

$166

avg/night

$166
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

We are proud of our Siesta Key Condo at Ebb Tide. This Florida Beach Rental is in the heart of Crescent Beach. Once you park your car there is no need to use a car for the rest of your stay. A short 1 1/2 block walk and your toes are enjoying the lush, white (quartz) sands of the crescent beach.The ...

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Property Type

Siesta Key Studio

Featured review

"A little piece of Paradise."

The condo was absolutely amazing, and very affordable. Perfect for a couple, so close to the bay and the beach. The condo had everything needed for our stay. Will definitely book again. I love going to ...

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

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

$281

avg/night

$281
avg per night
View Details

Key Amenities

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

About this property

*Calendar month rentals only*May-October (six-month lease) - $3500 per month plus utilities November & December - $6900 per month plus utilities January, February, & March - $8900 per month plus utilities April - $7900 per month plus utilities50% deposit upon booking, balance 90 prior ...

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Property Type

Siesta Key Bungalow

Featured review

"We Keep Coming Back"

It's all about The Lily Patch on Palm Island in the village of Siesta Key!!! We've love it so much that we've signed up again for 2021 (Winter #3) and sent in a donation to the neighborhood HOA this time. Bring ...

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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

$213

avg/night

$213
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 House
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms

Distance to beach: 1 miles to Turtle Beach

$385

avg/night

$385
avg per night
View Details

Key Amenities

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

About this property

New Listing Siesta Key, Florida !!100% 5 Star reviews on AirBnB and VRBO, save fees by booking direct through owner on this site. Discounts for multiple monthly stays.Available June, August, September and October and December 15, 2024 - January 18, 2025 Not available January 18 - May 16, 2025Hibiscus ...

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Property Type

Siesta Key House

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