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

$379

avg/night

$379
avg per night
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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 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
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Key Amenities

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

About this property

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

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Property Type

Siesta Key Condo

Featured review

"Perfect"

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

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Siesta Key Condo
2 BR | 2 BA | Sleeps 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
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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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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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Siesta Key Villa

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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 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
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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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Siesta Key Condo

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

$336

avg/night

$336
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • WiFi

About this property

Come enjoy our unique TWO MASTER BEDROOMS condo! BOTH master bedrooms have the very same beautiful ocean view, and each has it's own "private" access to the lovely lanai! Life doesn't get any better than this, on tropical Siesta Key!!! As you will tell from our pictures, we love the ...

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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

$367

avg/night

$367
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Get ready to be whisked away on a wild beach adventure at Siesta Key Beach - the crème de la crème of all beaches, with its shimmering quartz sand and sunset extravaganza! Tucked away on the third-floor corner is the ultimate luxurious hideaway, Unit 301. With two bedrooms, two full bathrooms, ...

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

$275

avg/night

$275
avg per night
View Details

Key Amenities

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

About this property

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

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Property Type

Siesta Key Condo

Featured review

"Just what we wanted."

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

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

$389

avg/night

$389
avg per night
View Details

Key Amenities

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

About this property

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

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Property Type

Siesta Key Condo

Featured review

"Beautiful Condo!"

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

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

Distance to beach: 300 feet to Siesta Key Beach

$349

avg/night

$349
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Pool
  • WiFi

About this property

Pack your bags and prepare to be swept off your feet by the jaw-dropping magnificence of Siesta Key Beach - ranked numero uno for its powder-soft quartz sand and sunset spectacles! Nestled on the third-floor corner, Unit 301 is a luxurious haven, boasting two bedrooms, two full bathrooms, and over 1220 ...

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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
1 BR | 1 BA | Sleeps 2 | Quick View
Sleeps 2, 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
  • Hot tub
  • Pool
  • WiFi

About this property

Welcome to your very own slice of paradise! This breezy 1-bed, 1-bath suite boasts over 820 sq ft of living space, all to yourself. Take a deep breath and soak up the sun on the fourth-floor balcony, peeking out over miles of stunning gulf coast. With a plush king-sized bed, a fully-loaded kitchen, 2 ...

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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
13 reviews

$400

avg/night

$400
avg per night
View Details

Key Amenities

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

About this property

This outstanding condo, A203, is on the second floor, accessible using the elevator or outside stairwell and is completely renovated with modern tile flooring throughout, updated kitchen and baths, and new furniture! The kitchen has granite counter tops with tiled back splash, and modern appliances including ...

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Property Type

Siesta Key Condo

Featured review

"Wish we could have stayed longer!"

We stayed on Turtle Bay and had a wonderful view of the Gulf from our second floor balcony. The condo was clean and the decor was fun to look at. They had so many extras available: laundry detergent, ...

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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 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 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 5 | Quick View
Sleeps 5, 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

Condo 4D offers the perfect beach vacation, with its stunning view of The Gulf and Siesta Key Beach from the fourth floor. This 1220 square foot condo features a beachy vibe that will beckon you to enjoy America's top-rated beach.The condo has two bedrooms and two full bathrooms, with the master ...

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Property Type

Siesta Key Condo

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

Distance to beach: 300 feet to Siesta Key Beach

$297

avg/night

$297
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Pool
  • WiFi

About this property

Beautiful views of the Gulf of Mexico's Siesta Key Beach. Dr. Beach's #1 rated beach in the U.S. can be seen from Crescent Royale's Unit 2E! This newly renovated (2024) and refurnished 2 bedroom, 2 bath condo is an end unit that features a wrap-around screened lanai that offers panoramic ...

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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

$300

avg/night

$300
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

This first-floor 1 Bedroom/1 Bath unit is ideally located just a few steps away from the highly acclaimed #1 Siesta Key Beach. Experience a stress-free day in the sun with all the necessary amenities provided, including chairs, an umbrella, towels, a cooler, and even a beach wheelie. All you need to bring ...

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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
27 reviews

Distance to beach: 0.1 miles to Siesta Key Beach

$265

avg/night

$265
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

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

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Property Type

Siesta Key Condo

Featured review

"Awesome rental in siesta key"

The. Condo is in a perfect location, within walking distance of the beach, close to restaurants and shopping and the pool was perfect. The condo was well decorated and equipped with everything we needed. ...

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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
12 reviews

Distance to beach: 0.2 miles to Siesta Key Beach

$295

avg/night

$295
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

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

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Property Type

Siesta Key Condo

Featured review

"Mullins review"

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

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

Distance to beach: 300 feet to Siesta Key Beach

$336

avg/night

$336
avg per night
View Details

Key Amenities

  • Pool

About this property

Attention beach lovers! You're in for a treat with our Condo 407, where relaxation is the order of the day. With 1220 sq. ft. of space, 2 bedrooms, and 2 baths, this condo is a slice of heaven. And its location? Just a hop, skip, and jump away from Siesta Key beach!Sleep like royalty in either ...

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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

$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 Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 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

Get ready to dive into a tropical paradise at Condo 512! This dreamy dwelling boasts drop-dead gorgeous views of The Gulf and Siesta Key Beach from its fourth-floor location, giving you a front-row seat to America's number one beach!With two bedrooms and two full bathrooms, this 1220 sq ft condo ...

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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

$366

avg/night

$366
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Welcome to Condo 312, the epitome of luxury beachfront living. This gold-rated condo boasts an array of amenities to ensure you have a memorable vacation. With two bedrooms, two baths, and an expansive 1,220 square feet of living space, its beauty is simply breathtaking. Notably, it's situated right ...

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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

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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
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

$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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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

$336

avg/night

$336
avg per night
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Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Get ready to visit Condo 415 at Crescent Royale. This condo has been stirring up a storm with guests and our team alike. This funky little gem has a cult following of returning visitors, so you better act fast!The kitchen is equipped with all the bells and whistles you'd expect from a five-star ...

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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
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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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Siesta Key Condo

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

Distance to beach: 300 feet to Siesta Key Beach

$385

avg/night

$385
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Pool
  • WiFi

About this property

We love our special hideaway on Siesta Key. Please come and share our lovely condo. The sunsets are magnificent and a walk on the beach to see the sunrise will leave you with a memory of a lifetime. Siesta time is the only time to enjoy yourself........come see what we mean. We welcome you to our home ...

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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

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

$199

avg/night

$199
avg per night
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Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Welcome to your own slice of heaven! Feast your eyes on stunning Gulf and Beach views from your swanky new condo, 305. This deluxe 1-bed, 1-bath pad spoils you with over 820 sq ft of pure bliss, including a king-size bed, sleeper sofa for two additional guests, a drool-worthy gourmet kitchen, 2 flat screens, ...

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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
4.9 rating on other travel sites

$413

avg/night

$413
avg per night
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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 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
1 BR | 1 BA | Sleeps 3 | Quick View
Sleeps 3, 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
  • Pool
  • WiFi

About this property

Welcome to the fabulous Condo 209 at Crescent Royale! This condo features 1-bedroom, 1-bathroom pad is spacious, boasting over 825 sq. ft. of living space, leaving you plenty of room to spread out and relax.The Master bedroom is home to a king-sized bed that will make you feel like royalty. And there's ...

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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

$329

avg/night

$329
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Escape to a serene paradise at Crescent Royale, Siesta Key Beach, and experience the luxurious accommodations of Unit 107. This elegant unit offers two bedrooms, two bathrooms, and a spacious 1,250 square feet of living space, meticulously prepared to cater to your every need and ensure your comfort.Located ...

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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

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
2 BR | 2 BA | Sleeps 5 | Quick View
Sleeps 5, 2 bedrooms, 2 bathrooms
1 review

Distance to beach: 300 feet to Siesta Key Beach

$397

avg/night

$397
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Pool
  • WiFi

About this property

Enjoy the inviting atmosphere in this comfortable corner unit located on the 6th floor with lots of natural light. There are panoramic views of the beaches and Gulf waters. Siesta Key Beach is public and life guarded. The free trolley ride to the Village can provide dining, nightlife, shopping, people ...

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Property Type

Siesta Key Condo

Featured review

"Amazing place"

Best service ever, everything there, beach play, umbrellas, fishing poles and more, just bring our food, 100% recommendable

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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!