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

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

Distance to beach: 300 feet to Siesta Key Beach

$329

avg/night

$329
avg per night
View Details

Key Amenities

  • Air conditioning
  • Oceanfront
  • Pool
  • WiFi

About this property

Sandcastles, sunrises, sunsets on Siesta Key! Experience the ultimate Siesta Key vacation with unit 509 - a stunning penthouse on Siesta Key Beach that offers the perfect blend of relaxation and luxury.Located on the top floor, this one-bedroom unit features 820 square feet of cozy comfort with breathtaking ...

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Property Type

Siesta Key House

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

Distance to beach: 100 feet to Crescent Beach

$430

avg/night

$430
avg per night
View Details

Key Amenities

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

About this property

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

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Property Type

Siesta Key Condo

Featured review

"Perfect"

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

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Siesta Key Condo
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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Siesta Key Condo

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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
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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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Siesta Key Condo

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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

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

Prepare to embark on an unforgettable beach escapade at Siesta Key Beach, the epitome of all beaches, with its sparkling quartz sand and stunning sunset views. Nestled away on the third-floor corner is the ultimate luxurious hideaway, Unit 3C. With two bedrooms, two full bathrooms, and 1220 sq. ft. of ...

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Property Type

Siesta Key Condo

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Siesta Key Condo
3 BR | 2 BA | Sleeps 7 | Quick View
Sleeps 7, 3 bedrooms, 2 bathrooms

Distance to beach: 300 feet to Siesta Key Beach

$452

avg/night

$452
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Pool
  • WiFi

About this property

Georgeous Gulf Views from this top floor unit which has a double wide lanai. Large, spacious unit that provides a retro environment that provides hollywood style for all to enjoy. You'll be able to interact with the beach, view and Gulf of Mexico as you view it all from your 7th floor. Come and Enjoy!

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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

$329

avg/night

$329
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Prepare to be whisked away to a beachy paradise penthouse Condo 508 in stunning Siesta Key Beach! This top-floor one-bedroom unit offers up a whopping 820 square feet of pure relaxation and cozy comfort. With Gulf and beach views that'll make your heart skip a beat, you'll be feeling like a ...

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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

$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, FL Crescent Arms Condominium Complex: Located directly on world famous Crescent Beach these Siesta Key beachfront ...

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Property Type

Siesta Key Condo

Featured review

"Beach and ocean waves"

The condo was super nice. The master bedroom mattress was amazing for a rental. So often I feel like they are hard as rocks but this one wasn’t. The second bedroom had similar mattress but they were not ...

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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
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 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
  • Pool
  • WiFi

About this property

Indulge in a perfect beach vacation at Condo 511, offering stunning views of The Gulf and Siesta Key Beach from the fourth floor. This 1220 square foot condo features 2 bedrooms, 2 full bath rooms and has a relaxing and casual beachy vibe, inviting you to unwind and enjoy America's top-rated beach.The ...

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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

Distance to beach: 300 feet to Siesta Key Beach

$573

avg/night

$573
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Pool
  • WiFi

About this property

Enjoy the only three bedroom unit, with a spectacular view of Siesta Beach. On a clear day you can see all the way to Venice. Our spacious living room and dining room are very easy to entertain while you are here. Come and share our fabulous sunsets and calming sounds of the Gulf of Mexico.

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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

$292

avg/night

$292
avg per night
View Details

About this property

Condo 205 is an exquisite 1 bedroom, 1 bathroom, second-floor unit that offers over 820 square feet of comfortable living space. The fully stocked kitchen featuring full-size appliances provides the perfect opportunity to showcase your culinary skills.With a king-sized bed, the bedroom is designed ...

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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

$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
44 reviews

$400

avg/night

$400
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
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms
4.6 rating on other travel sites

$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, FL Crescent 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
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
View Details

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
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
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms

$392

avg/night

$392
avg per night
View Details

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
2 BR | 2 BA | Sleeps 5 | Quick View
Sleeps 5, 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

Prepare to be awestruck by the sheer beauty of Siesta Key Beach - your perfect vacation destination. The breathtaking panoramic view of the beach from unit 502 at Crescent Royale Condominiums will transport you to a paradise-like setting.Recently renovated, this unit exudes a modern and relaxed beach ...

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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

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

Distance to beach: 300 feet to Siesta Key Beach

$351

avg/night

$351
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Pool
  • WiFi

About this property

Experience the ultimate Siesta Key vacation with the picturesque unit 515 at Crescent Royale. This spacious 2-bedroom and 2-bathroom condo offers a serene ambience with stunning views of sunrise and sunset from the screened lanai. The unit features traditional Florida decor and comes fully equipped with ...

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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 Apartment
9 BR | 9 BA | Sleeps 25 | Quick View
Sleeps 25, 9 bedrooms, 9 bathrooms
3 reviews

$315

avg/night

$315
avg per night
View Details

Key Amenities

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

About this property

Our seven apartment beach house is located 100 yards from the beach at Access #7 and one-block from the tropical Village of Siesta Key. Heated pool and spa along with our poolside surfboard bar and barbecue give our guests many choices to very their daily routine. Our 1st and 2nd floor above ground level ...

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Property Type

Siesta Key Apartment

Featured review

"Best place in the keys"

This place is one of a kind. It has everything you need. Our family rents out the entire place every couple years. The location is amazing...right by the village and beach. The rooms are clean and bug free!!! ...

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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
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

$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 | 1.5 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 1.5 bathrooms
32 reviews
owner special
Owner special: Spring Break Dates available

Distance to beach: 200 yards to Crescent Siesta Key Beach

$286

avg/night

$286
avg per night
Owner special:
Spring Break Dates available

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 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

Welcome to Condo102 at Crescent Royale - a ground floor 2-bedroom, 2-bathroom condo boasting 1,210 square feet of beachfront opulence. The master suite is furnished with a king-sized bed, while the guest room features two queen-sized beds, making it the ideal location for families or couples seeking a ...

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Property Type

Siesta Key Condo

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Siesta Key House
4 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 3 bathrooms
1 review

Distance to beach: 300 feet to Siesta Key Beach

$809

avg/night

$809
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

This is a newly remodeled developers double wide four bedroom three and half bath penthouse unit with over 2,000 square feet that offers spacious living and entertaining areas for gatherings of family and friends with stunning panoramic views of the beach from its seventh floor location. The two master ...

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Property Type

Siesta Key House

Featured review

"Excellent vacation stay"

The condo and property were fantastic. The location and view of Siesta Key were amazing. This condo was great for our family vacation and the swimming pool was very clean and spacious. Definitely want ...

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

$319

avg/night

$319
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 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 Villa
4 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 2 bathrooms
12 reviews

$375

avg/night

$375
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

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

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Property Type

Siesta Key Villa

Featured review

"Great Space."

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

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Siesta Key House
4 BR | 2.5 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 2.5 bathrooms
10 reviews

$686

avg/night

$686
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 Getaway!"

We SO enjoyed our stay there! Our stay was to celebrate a milestone birthday of our sister and we couldn't have asked for a better spot! Our main goal was to relax, catch up and enjoy the beautiful beach ...

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

$327

avg/night

$327
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
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
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
View Details

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 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 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

Unit 1D is a luxurious ground floor unit offering two bedrooms, two bathrooms, and 1,210 square feet of living space. The décor is traditional yet sophisticated, and the open concept kitchen is fully-equipped, making it a gourmet's delight. The apartment is ideally situated just steps away ...

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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
9 reviews

$254

avg/night

$254
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

$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
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

Show less

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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Show less

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

$327

avg/night

$327
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Welcome to the magnificent Condo 306 at Crescent Royale! This exquisite residence boasts a spacious 2-bedroom, 2-bathroom floor plan that spans over 1225 sq. ft. of living space, providing ample room for relaxation and entertainment.The Master bedroom features a king-sized bed that exudes a regal ...

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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

$304

avg/night

$304
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Get ready to soak up the sun and sea with Unit 309, a gorgeous 1-bed, 1-bath condo with over 820 square feet of pure bliss! Breathe in the salty air, dip your toes in the white quartz sand, and watch the sunrise from your screened lanai while sipping your morning coffee. When the sun sets, get ready for ...

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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
4.9 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, FLTop beachfront unit at Fisherman's Cove!! Fisherman's Cove is a very rare Siesta Key condo where every unit has direct, unobstructed, ...

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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!