Siesta Key Vacation Rentals

(250 rentals)
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Siesta Key Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms

Distance to beach: 300 feet to Siesta Key Beach

$348

avg/night

$348
avg per night
View Details

Key Amenities

  • Pool

About this property

Welcome to Condo 3E, located in the serene paradise of Siesta Key Beach. This beach-themed haven is designed to transport you to a world of relaxation and tranquility. With 1220 sq.ft of living space, two bedrooms, and two baths, you'll have ample space to unwind and rejuvenate.The master bedroom ...

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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

$329

avg/night

$329
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Welcome to Paradise, where you can revel in the breathtaking views of the Gulf.Unit 115 boasts 2 bedrooms, 2 baths, and a spacious 1,250 square feet of living space. With a screened-in lanai featuring a rear exit, the unit exudes a cottage-like feel rather than a standard condo.Siesta Key offers ...

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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

$371

avg/night

$371
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Siesta Key - Gulf-Front Retreat - 2 BR - Free Boat Docks - Upscale Located Next to Turtle Beach on the Southern End of Siesta Key, Sarasota, FL Fisherman's Cove is a very rare Siesta Key condo where every unit has direct, unobstructed, full Gulf views. The building is one of the closest condos ...

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Property Type

Siesta Key Condo

Featured review

"GREAT!!"

These people are great , have stayed there before and will again.clean good service nice pool right on the gulf.

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

Distance to beach: 300 feet to Siesta Key Beach

$329

avg/night

$329
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Stop the vacation rental search, the ultimate getaway is here! Get ready to sink your toes into the sand at Crescent Royale's vibrant community, where unit 106 is waiting for you with 2 bedrooms and 2 bathrooms, beautifully decorated with over 1250 sq. ft. of living space.The screened-in lanai ...

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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
8 reviews

$365

avg/night

$365
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 Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms

Distance to beach: 300 feet to Siesta Key Beach

$367

avg/night

$367
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Welcome to Condo 303, the perfect home to experience and cherish your dream beach vacation at the number one rated beach in America - Siesta Key.This recently updated 2 bedroom and 2 bathroom condo boasts a traditional decor vibe and a fully equipped gourmet kitchen featuring Bosch appliances and ...

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Siesta Key Condo

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

Distance to beach: 300 feet to Siesta Key Beach

$338

avg/night

$338
avg per night
View Details

Key Amenities

  • Air conditioning
  • Oceanfront
  • Pool
  • WiFi

About this property

Prepare to be spellbound by the magnificent Condo 304! This four-person stay has undergone recent renovations, including state-of-the-art furniture, modern gadgets, and two 55-inch smart TVs. The accommodation offers a king bed, queen bed, and full sleeper sofas, plus a pack-n-play for families with young ...

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Siesta Key Condo

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

Distance to beach: 20 yards to Crescent Beach, Siesta Key

$345

avg/night

$345
avg per night
View Details

Key Amenities

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

About this property

Unit 113 is one of the largest, 1 bedroom hi-rise units in Horizons West, Siesta Key, Florida and has recently undergone a full renovation by a Chicago designer. The interior was fully demolished and rebuilt. No detail or expense was spared in completing the perfect beach condo: large panoramic ocean ...

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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

$407

avg/night

$407
avg per night
View Details

Key Amenities

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

About this property

Fisherman's Cove Condominiums have the best Location on Siesta Key! It is surrounded by water with the Gulf of Mexico on the west side and a private lagoon that leads to the inter-coastal waterway (ICW) on the east side. Swim, surf, boat, kayak, paddle board, fish, gather sea shells and shark’s ...

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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

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

$234

avg/night

$234
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
1 BR | 1 BA | Sleeps 3 | Quick View
Sleeps 3, 1 bedroom, 1 bathroom

Distance to beach: 300 feet to Siesta Key Beach

$311

avg/night

$311
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Experience an idyllic vacation on Siesta Key with this capacious one-bedroom suite, extending over 820 sq ft. Enjoy the breathtaking views of the Gulf Coast from the fourth-floor balcony, bask in the sunshine, and revel in the serene atmosphere. This suite boasts a comfortable king-sized bed, two flat-screen ...

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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

Distance to beach: 300 feet to Siesta Key Beach

$367

avg/night

$367
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Get ready to soak up some serious rays in our beachy haven, Condo 3D, located in the paradise of Siesta Key Beach! With 1220 sq. ft. of space, 2 bedrooms, and 2 baths, you'll have plenty of room to stretch out and catch some Z's.This beach-themed unit will transport you to a world of tranquility, ...

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Property Type

Siesta Key Condo

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

$350

avg/night

$350
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 Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms

$208

avg/night

$208
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Renovated 2BR (one queen size & 2 single beds) 2 Bathrooms 2nd floor condo and with all the amenities of a comfortable home. Located in White Sands Village with 7 acres of lush tropical surroundings & paved stones drive and covered parking, newly installed luxury wood-like flooring a comfortable ...

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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

$398

avg/night

$398
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

CRESCENT ARMS - Siesta Key Beachfront Vacation Condos on Crescent Beach (Two Bedroom Beachfront Unit for Rent)Located Directly on Crescent Beach on the middle of Siesta Key, Sarasota, FLCrescent Arms Condominium Complex: Located directly on world famous Crescent Beach these Siesta Key beachfront ...

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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

Distance to beach: 300 feet to Siesta Key Beach

$266

avg/night

$266
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Pool
  • WiFi

About this property

Welcome to Condo 204, a 1-bedroom, 1-bathroom unit that exudes a charming beachy cottage atmosphere with its blue interior, setting the stage for the ultimate beach retreat. The bedroom boasts a king-sized bed, fit for royalty, while the living room features a sofa sleeper, accommodating an additional ...

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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

Distance to beach: 300 feet to Siesta Key Beach

$373

avg/night

$373
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Pool
  • WiFi

About this property

Welcome to Condo 505, an opulent vacation home located in the Crescent Royale Condominiums at the stunning Siesta Key! This unit is highly sought after and promises breathtaking beachfront views over America's top-rated beach, offering 1220 sq ft of luxury living space.With two cozy bedrooms, ...

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Property Type

Siesta Key Condo

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

Distance to beach: 300 feet to Siesta Key Beach

$290

avg/night

$290
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Welcome to the beach lover's paradise, Condo 409! This little treasure trove offers you front-row seats to the Gulf of Mexico's breathtaking views from the Siesta Key Beach. With over 820 sq. ft of living space, this 1-bedroom and 1-bath condo flaunt a king-sized bed, a queen-sized sleeper sofa, ...

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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

Distance to beach: 300 feet to Siesta Key Beach

$336

avg/night

$336
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Prepare to bask in the breathtaking Gulf of Mexico sunsets from your very own private beach retreat! Unit 201 is a dream come true, complete with two inviting bedrooms and two modern bathrooms spread across 1210 square feet of pure luxury on the second floor. This condo's exclusive corner positioning ...

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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

Distance to beach: 300 feet to Siesta Key Beach

$379

avg/night

$379
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Experience the ultimate in tranquil living at Condo 4 E, the most idyllic location in Siesta Key. This two-bedroom, two-bathroom condo boasts over 1220 square feet of living space, complete with breathtaking full Gulf and beach views.This bright, airy, end unit is the perfect retreat for relaxation, ...

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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

Distance to beach: 300 feet to Siesta Key Beach

$353

avg/night

$353
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Check out this completely renovated 2nd floor condo! Unit 203 has had a complete facelift! This open floor plan allows beach visibility as soon as you walk in the door. New everything, furniture, TVs, stainless steel appliances, flooring, remodeled bathrooms and kitchen.Enjoy the beach from the lanai ...

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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

$380

avg/night

$380
avg per night
View Details

Key Amenities

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

About this property

This vacation rental condo is directly on the beach and is direct oceanfront (Gulf-front). Unfortunately, there are properties that falsely claim to be beachfront / oceanfront. We encourage travelers to ask property owners to verify those claims. We are excited to announce that B108 has recently been ...

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Property Type

Siesta Key Condo

Featured review

"Outstanding"

This is our third year in a row staying at Fishermans Cove. Our first year we were in a second floor condo these last two years we had ground floor and wouldn’t have it any other way. Everything is spotless, ...

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

Distance to beach: 300 feet to Siesta Key Beach

$307

avg/night

$307
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Experience the ultimate beach escape at Unit 110, just steps away from Siesta Key Beach's dazzling, white quartz sand.This 2-bedroom, 2-bathroom unit offers approximately 1,250 square feet of charming living space. Upon entry, you'll be welcomed by a cozy living and dining area that flows ...

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Property Type

Siesta Key Condo

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

Distance to beach: 300 feet to Siesta Key Beach

$348

avg/night

$348
avg per night
View Details

Key Amenities

  • Pool

About this property

Step into the grand Condo 307 at Crescent Royale and prepare to be wowed! This slice of paradise flaunts a massive 2-bed, 2-bath floor plan that sprawls over 1225 square feet. Kick back and relax in style in this spacious abode, perfect for entertaining or just lazing around.The main bedroom is a ...

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Property Type

Siesta Key Condo

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

Distance to beach: 300 feet to Siesta Key Beach

$347

avg/night

$347
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Get ready to fall in love with Unit 1C, where Gulf of Mexico's stunning views and warm sandy beaches welcome you with open arms! This 2-bed, 2-bath unit is a spacious 1210 sf. - the perfect slice of paradise.The kitchen is a chef's dream, stocked with high-end appliances, cookware, and utensils. ...

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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

Distance to beach: 300 feet to Siesta Key Beach

$379

avg/night

$379
avg per night
View Details

Key Amenities

  • Pool
  • WiFi

About this property

Get ready to be swept off your feet by the ultimate beach paradise - Siesta Key Beach! With its sparkling quartz sand and gorgeous sunset views, this beach is THE place to be. And the cherry on top? You'll be staying in the most luxurious beach vacation home on the fourth floor, Unit 403.This ...

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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

Distance to beach: 300 feet to Siesta Key Beach

$405

avg/night

$405
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

We love our view and we're sure that you will too. Walk on the beach or to the village for that tropical vacation of a lifetime. We're sure that you will love our little portion of paradise and agree that there is nothing like the sunrises and sunsets that we have to offer on Siesta Key. Start ...

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Property Type

Siesta Key Condo

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Siesta Key Villa
2 BR | 2 BA | Sleeps 7 | Quick View
Sleeps 7, 2 bedrooms, 2 bathrooms

Distance to beach: 0.0 miles to Siesta Key

$383

avg/night

$383
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Pool
  • WiFi

About this property

Escape to your private oasis on Siesta Key! This spacious villa offers the best of both worlds: direct access to the #1-rated Siesta Key Beach through your own private beach area, and stunning views of the Intracoastal Waterway where you can watch boats go by or launch your own kayak.Unwind in comfort ...

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Property Type

Siesta Key Villa

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Siesta Key Condo
3 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 2 bathrooms

Distance to beach: 300 feet to Siesta Key Beach

$715

avg/night

$715
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Prepare to be impressed by the breathtaking luxury of this 5th-floor penthouse. Boasting three bedrooms, three bathrooms, and 1,700 square feet of beachfront living, this unit is sure to delight.Recently renovated, this penthouse features an expansive lanai, complete with all of the amenities you ...

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Property Type

Siesta Key Condo

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Siesta Key Condo
3 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 2 bathrooms
4.6 rating on other travel sites

$413

avg/night

$413
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Beachfront Condo - Three Bedroom - Heated Pool - Free Boat Docks - Upscale - Siesta KeyLocated Next to Turtle Beach on the Southern End of Siesta Key, Sarasota, FL Fisherman's Cove is a very rare Siesta Key condo where every unit has direct, unobstructed, full Gulf views. The building is one of ...

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Property Type

Siesta Key Condo

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

$218

avg/night

$218
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

The Siesta Key vacation condo rental is a one bedroom / one bathroom individually owned condominium at the Gulf and Bay Club Bayside and is furnished with the basic household items necessary for normal living. This unique Old Key West style condo is fully equipped with an emphasis on vacation living. ...

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Property Type

Siesta Key Condo

Featured review

"March Getaway!"

Siesta Key was very beautiful and a great place to visit. The accommodations were very nice, clean and comfortable. We hope to visit this area again next year.

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

Distance to beach: 0.1 miles to Crescent Beach Siesta Key

$300

avg/night

$300
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Welcome to The Anchorage Yacht and Tennis Club across from the beautiful sands of Crescent Beach on Siesta Key. Sitting directly on the intercoastal waterway where you can park your boat, jet ski, kayak, and paddleboard. This complex has an Olympic size pool, three lighted tennis courts, pickleball nets. ...

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Property Type

Siesta Key Condo

Featured review

"Unit 403"

The place is absolutely beautiful. Great views and amenities! Close to walking distance to most things. Would definitely stay here again!

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

$806

avg/night

$806
avg per night
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 Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms

Distance to beach: 300 feet to Siesta Key Beach

$336

avg/night

$336
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Get ready to have your socks knocked off while enjoying breathtaking ocean views from this newly renovated condo.This 2 Bedroom 2 Bathroom upgrade includes all new LVP floors throughout, fresh paint and trim, upgraded Whirlpool stainless steel appliances, a Reme Halo all in one Whole Home Air Purification ...

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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

Distance to beach: 300 feet to Siesta Key Beach

$278

avg/night

$278
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to Unit 104 at Crescent Royale! Only a hop, skip and jump (well, technically 100 steps away) from the pristine Siesta Key Beach where you should be prepared to get swept off your feet by the jaw-dropping, sunset views from your very own screened lanai.This cozy 1 bedroom, 1 bath unit boast ...

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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

Distance to beach: 300 feet to Siesta Key Beach

$364

avg/night

$364
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Welcome to Unit 5B at Crescent Royale, an idyllic vacation destination. This charming unit boasts 2 bedrooms, 2 bathrooms, and over 1200 square feet of living space, all offering stunning views of the Gulf. The fully stocked kitchen features full-sized appliances, and all you need to bring is your culinary ...

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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
2 reviews

$340

avg/night

$340
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

"Cold escape"

We always enjoy our stay at Gulf and Bay Bayside!!! Condos are perfect! We always meet new people who have become friends and can’t wait to see them again next year!!!

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

Distance to beach: 300 feet to Siesta Key Beach

$361

avg/night

$361
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Prepare to feel regal as you step into this luxurious condo, situated in the heart of Florida's tropical paradise. Imagine waking up to the serene sound of waves crashing onto the shore, sipping coffee while admiring the picturesque blue ocean from your window. Our condo is the perfect place to live ...

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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
2 reviews

$371

avg/night

$371
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Siesta Key - Gulf-Front Retreat - 2 BR - Free Boat Docks - Upscale Located Next to Turtle Beach on the Southern End of Siesta Key, Sarasota, FL Fisherman's Cove is a very rare Siesta Key condo where every unit has direct, unobstructed, full Gulf views. The building is one of the closest condos ...

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Property Type

Siesta Key Condo

Featured review

"Beautifully renovated beach condo"

The condo contained anything and everything need to have a wonderful vacation. The view of the ocean was spectacular.

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

Distance to beach: 300 feet to Siesta Key Beach

$392

avg/night

$392
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Our condo is located in a beautiful complex with a wonderful pool to relax by. The sunrises will make your vacation one that you will never forget. Come and leave your footprints on the whitest sand in Southwest Florida, create memories of a lifetime and enjoy your visit in our home in paradise. Come ...

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Property Type

Siesta Key Condo

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

Distance to beach: 300 feet to Siesta Key Beach

$528

avg/night

$528
avg per night
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Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • WiFi

About this property

The unforgettable views from this top floor unit will surely have you coming back and telling your friends about. Siesta Key and Crescent Royale's beach front rentals. Hope you are here to have that much needed vacation. Relax, enjoy the spectacular Sunsets and Beach life views from this newly renovated ...

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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

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

$392

avg/night

$392
avg per night
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Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Stunning views of the Gulf of Mexico's Siesta Key Beach. Dr. Beach's #1 rated beach in the U.S." and its world renowned white quartz sand is only steps from vacationing at Crescent Royale's Unit 5A! This newly (2021) renovated and refurnished 2 bedroom/2 bath "Beachy" condo ...

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Property Type

Siesta Key Condo

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

Distance to beach: 20 yards to Crescent Beach, Siesta Key

$505

avg/night

$505
avg per night
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Key Amenities

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

About this property

Unit 608 is a large 3 bedroom, 2 bath high-rise unit in Horizons West, Siesta Key, Florida. The unit has recently undergone a complete makeover by a Chicago designer. The interior was fully demolished and rebuilt. No detail or expense was spared in completing the perfect beach condo: large panoramic ocean ...

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Property Type

Siesta Key Condo

Featured review

"Wonderful place to stay!"

Recently, we stayed at a Fisherman’s Cove for Spring Break. What a wonderful place to stay! Close to the ocean/beach and the condo had everything we needed!

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

$371

avg/night

$371
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Siesta Key - Gulf-Front Retreat - 2 BR - Free Boat Docks - Upscale Located Next to Turtle Beach on the Southern End of Siesta Key, Sarasota, FL Fisherman's Cove is a very rare Siesta Key condo where every unit has direct, unobstructed, full Gulf views. The building is one of the closest condos ...

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Property Type

Siesta Key Condo

Featured review

"Beautiful Condo in a nice quiet area a stone's throw from the beach."

We loved this condo. It was beautiful, newly refurbished and so comfortable. More like a nice family home than just a rental. We loved sitting in the sun on the lanai watching the birds and the beach. ...

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

Distance to beach: 300 feet to Siesta Key Beach

$307

avg/night

$307
avg per night
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Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Welcome to this spacious 1 Bedroom 1 Bath unit, covering over 820 square feet of open living space. Located on the fourth floor, this unit comprises a king-sized bed, a fully equipped kitchen, a full bathroom, 2 flat-screen TVs, and a beach kit that includes chairs, a beach umbrella and towels.The ...

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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

Distance to beach: 300 feet to Siesta Key Beach

$348

avg/night

$348
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Pool
  • WiFi

About this property

Welcome to Paradise, where you can bask in the glory of Siesta Beach, the number one beach in the United States, just 100 steps away from your doorstep! Condo 311 offers 2 bedroom and 2 full Bathrooms featuring over 1220 sf of open living space, with panoramic views of the gulf. Imagine enjoying your ...

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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

Distance to beach: 300 feet to Siesta Key Beach

$329

avg/night

$329
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Prepare yourself for a luxurious experience in your very own slice of paradise! Envision yourself savoring a refreshing beverage while taking in stunning sunsets from your private screened lanai, situated just a short distance from Siesta Key's pristine sugar sand beach. After a day filled with fun ...

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Property Type

Siesta Key Condo

Show less

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

Distance to beach: 300 feet to Siesta Key Beach

$336

avg/night

$336
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Pool
  • WiFi

About this property

Welcome to Condo 402, your ticket to paradise! Get ready to be swept away by stunning views of the Gulf of Mexico from the Master Bedroom and screened-in lanai. With over 1220 square feet of living space, there's plenty of room to soak up the sunshine and catch some z's.The Master Bedroom ...

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Property Type

Siesta Key Condo

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

Distance to beach: 300 feet to Siesta Key Beach

$367

avg/night

$367
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Pool
  • WiFi

About this property

Get ready to soak up the sun and surrender to the ultimate beachside escape! This third-floor 2 BR 2 BR condo will have you feeling like royalty with its stunning view of the Gulf of Mexico's pristine beaches. It's a year-round oasis where every moment will take your breath away!The open ...

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Property Type

Siesta Key Condo

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Siesta Key Vacation Rentals

Siesta Key Weather

 | 

7122°  5111°
JANUARY
Ocean 6418°
7423°  5412°
FEBRUARY
Ocean 6518°
7725°  5814°
MARCH
Ocean 6719°
8127°  6217°
APRIL
Ocean 7323°
8630°  6820°
MAY
Ocean 7826°
8932°  7323°
JUNE
Ocean 8228°
9133°  7423°
JULY
Ocean 8530°
9133°  7524°
AUGUST
Ocean 8730°
8932°  7323°
SEPTEMBER
Ocean 8529°
8529°  6719°
OCTOBER
Ocean 8228°
7926°  6016°
NOVEMBER
Ocean 7524°
7423°  5412°
DECEMBER
Ocean 6921°

Find the Beach Vacation of a Lifetime with Siesta Key Vacation Rentals


Interested in a beach vacation for your next spring break or a long weekend away? Though the great state of Florida is known for its many scenic beach towns, there are some that cater more to those looking for a quiet, relaxing trip and some that are perfect for an exciting vacation full of non-stop fun in the sun. What if you could find a beach city that offers the best of both worlds for a truly well-rounded vacation? Enter Siesta Key vacation rentals. 

Nestled just south of Sarasota, Siesta Key, FL, is a spirited city along the Gulf Coast that offers just as many opportunities for R&R as it does for nightlife, watersports, and unforgettable adventures in the great outdoors. Though the island of Siesta Key itself is only about eight miles long, it’s jam-packed with enticing restaurants, unique shops, and glittering white sand beaches as far as the eye can see. 

As a major vacation destination along Florida’s Gulf Coast, there are many hotel options to choose from during your stay, with varying proximities to the beach. However, if you’re looking for a truly immersive experience during your trip to Siesta Key, you won’t get it at a crowded commercial hotel! 

Browse Siesta Key vacation rentals from FloridaRentals to find the perfect rental home for your beach vacation. Whether you’re looking for a sunny, romantic getaway for you and a loved one, or you’re bringing the whole family along, you’re sure to find an incredible property. Look for one that offers authentic local architecture, plenty of space to spread out during your downtime, and close proximity to all of the best features the city has to offer.

Siesta Key, Florida Travel Tips


There’s a reason why oceanside Florida cities like Siesta Key tend to be popular destinations during springtime. While temperatures may be warmest on average in the summer months, this time of year also has the highest levels of precipitation and humidity. Unfortunately, this makes it more difficult to enjoy outdoor activities. 

In mid to late spring, temperatures in the air and water are warm and comfortable without too much rain or humidity expected. This makes it easy to take part in all of your favorite pastimes, including surfing, boating, wakeboarding, or simply catching some rays on the sand. 

The closest airport to Siesta Key is the Sarasota/Bradenton International Airport, which lies around 11 miles north of the city center. Most visitors will fly into this airport for its easy access, though the area can also be reached relatively quickly by way of the Tampa International Airport.

How to Spend Your Vacation to Siesta Key House Rentals


It’s no surprise that most Siesta Key vacationers spend more time at the beach than anywhere else during their visits. The most popular beach destination is Siesta Key Beach, which was ranked the #1 Beach in the U.S. by TripAdvisor’s Traveler’s Choice Awards in 2020. The gentle waves, powdery white sand, ample parking, and plentiful concession stands are just some of the reasons why many visitors choose to lounge their day away at Siesta Key Beach. 
Those who are interested in an unforgettable outdoor experience shouldn’t miss out on a trip out on the water with Adventure Kayak Outfitters. You’ll have the choice of a guided kayak tour of the nearby Exotic Mangrove Tunnels or a kayak rental to make your own adventure. You’re sure to spot some incredible wildlife like dolphins, exotic birds, and manatees along the way.

Yearly Events in Siesta Key


Siesta Key is closely linked with the nearby city of Sarasota. The two cities share many of their annual events, creating even bigger and better celebrations for locals and tourists alike to enjoy. 

One annual event that’s already become a mainstay in the local culture is the Annual Downtown Sarasota Craft Festival. This unique arts and crafts show features a wide variety of media, including pottery, paintings, jewelry, photography, and much more, alongside the scenic white-sand beaches. Visitors can peruse and purchase unique wares from local artisans, including soaps, spices, plants, and even kettle corn. 
Runners visiting Siesta Key can get in a great workout while supporting a great cause at the Annual Andrew Monroe Memorial Scholarship 5K Run/Walk. All funds raised during this event are donated to the Sarasota Community Foundation Scholarship, which helps local athletes train to their full potential and achieve their goals.  

Best Eats Near Siesta Key Rentals


Whether you’re in need of some casual seaside grub for the family after a long day at the beach or looking forward to a romantic date night with your significant other, Siesta Key has a huge variety of delicious and eclectic eateries fit for every taste and occasion. 

For a hearty steak, you can’t do much better than Summer House Steak & Seafood. This stylish eatery offers sustainably sourced steaks alongside a variety of unique sides, salads, beverages, and desserts that are sure to satisfy. Additionally, Summer House offers a full menu of seafood dishes. It takes full advantage of the city’s close proximity to fresh seafood and offers plenty of surf and turf options for hungry visitors. 

Island House Tap and Grill is a local favorite for casual yet memorable eats in Siesta Key. With a varied menu that includes everything from tacos to burgers to ceviche, as well as plenty of refreshing cocktails, you’re sure to enjoy a delicious and satisfying dinner with your family.


FAQ

How many vacation rentals are there in/around Siesta Key?

There are 250 Siesta Key vacation rentals available on FloridaRentals.com. From condo rentals to house rentals and beyond, find a unique vacation rental for you to enjoy a memorable vacation in Florida.

How much does it cost to rent a vacation rental in Siesta Key?

There are vacation rentals available in Siesta Key for as low as $139 per night with an average price per night of $361.

Can I find a vacation rental in Siesta Key?

Yes, you can find vacation rentals in Siesta Key close to Sieta Beach, Turtle Beach and Crescent Beach. Don't forget to stop in to Point of Rocks or Siesta Farmer's Market.

Do any vacation rentals in Siesta Key have a pool?

Yes, there are 46 vacation rentals with a pool in Siesta Key on FloridaRentals.com. Search using our filters and book one for your next vacation!

Are any Siesta Key vacation rentals on the ocean?

There are 50 oceanfront rentals in Siesta Key available on FloridaRentals.com. Use our filters to search and book yours today!