Siesta Key Vacation Rentals

(238 rentals)
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1 BR | 1 BA | Sleeps 4 | Quick View

$126

avg/night

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Key Amenities

  • Pet friendly

About this property

Quaint 1 bedroom bungalow with Murphy Bed that folds into the wall during the day providing additional living space. Living room w/leather furniture, french doors opening to a private brick patio. 2 TV's with DVD players. Kitchen offers a mini convection oven w/built in rottiserie for up to full ...

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Property Type

Siesta Key Condo

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3 BR | 2 BA | Sleeps 6 | Quick View

2

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

$381

avg/night

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool
  • Private pool

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

"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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3 BR | 2 BA | Sleeps 8 | Quick View

1

$243

avg/night

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Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool

About this property

20% OFF DECEMBER 2023!!! WELCOME TO PARADISE! COME RELAX IN THIS BEAUTIFUL 3 BEDROOM / 2 BATH GRAND CANAL HOME LOCATED IN THE QUIET NEIGHBORHOOD OF SIESTA ISLES. THIS FABULOUS REMODELED HOME FEATURES A CUSTOM GOURMET KITCHEN AND OPEN FLOOR PLAN PERFECT FOR ENTERTAINING. HIGH-SPEED INTERNET AVAILABLE, ...

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Property Type

Siesta Key House

"522 Canal Rd"

Great vacation rental home with tile floors throughout making it a perfect beach home. The house has four bedrooms three of which have their own private, full bathroom. Siesta-4-Rent Management was great ...

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5 BR | 3.5 BA | Sleeps 15 | Quick View

1

$796

avg/night

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Key Amenities

  • Air conditioning
  • Private pool

About this property

This 3400 sq ft., 5 Bedroom 3 Bath, Townhome Offers, Private heated pool- **please keep in mind the pool is refreshing, but has limited space for larger parties. Many balconies overlooking the pool. Beautiful custom kitchen, with Granite and Stainless. (REVISED LAYOUT of the HOUSE : Effective: Oct. 2019 ...

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Property Type

Siesta Key Condo

"Vacational stay"

This was a pleasant experience with the house and the pool, walking distance from the beach and the attractions, restaurants, shopping, etc: Very happy with the house: being big enough to accommodate ...

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2 BR | 2 BA | Sleeps 6 | Quick View

$385

avg/night

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Key Amenities

  • Oceanfront
  • Pool

About this property

SPECTACULAR VIEWS FROM THIS 2 BEDROOM / 2 BATH BEACHFRONT, GROUND FLOOR UNIT LOCATED IN THE CASA MAR COMPLEX WITH THE WORLD FAMOUS SIESTA KEY BEACH JUST A FEW FEET AWAY. THE CASA MAR COMPLEX OFFERS 2 POOLS, TENNIS, WIFI, (SIESTA 4- RENT DOES NOT OFFER TECH SUPPORT), COMMUNITY LAUNDRY ROOM, AND 1 COVERED ...

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Property Type

Siesta Key Condo

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1 BR | 1.5 BA | Sleeps 3 | Quick View

$351

avg/night

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Key Amenities

  • Air conditioning

About this property

**Any advertised discounts on website do not apply to this unit*** UNIQUE 1 BEDROOM TOWNHOUSE OVERLOOKING THE BEACH, 1 BLOCK TO SIESTA VILLAGE, 3 STORY UNIT WITH GARAGE ON 1ST FLOOR AND WASHER/DRYER, BALCONY, MEXICAN TILE FLOORS, KITCHEN, SPIRAL STAIRCASE TAKES YOU TO THE MASTER SUITE ON THE 3RD FLOOR, ...

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Property Type

Siesta Key Condo

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2 BR | 2 BA | Sleeps 4 | Quick View

$153

avg/night

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Key Amenities

  • Air conditioning
  • Pool

About this property

Harbor Towers 2nd floor unit located a few blocks south of the Siesta Public beach. Beautiful property located on the intercoastal. Pool and tennis, propane grills and coin laundry on each floor and elevator. NO smoking in unit and NO pets. Units sleeps 4, 1 King and 2 twins. 2 Week min. CLEANING FEE ...

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Property Type

Siesta Key Condo

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2 BR | 2 BA | Sleeps 6 | Quick View

$310

avg/night

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Key Amenities

  • Air conditioning
  • Pool

About this property

BREATHTAKING, DIRECT OCEANFRONT, 2 BEDROOM / 2 BATH UNIT WITH PANORAMIC VIEWS OF THE BEACH AND SARASOTA SKYLINE. GRANITE COUTERTOPS, TILE FLOORS IN KITCHEN, BATHS and LIVING ROOM, AND WOOD FLOORING IN BEDROOMS. LEATHER FURNITURE, 3 FLAT SCREEN T.V.'S ( 65 LIV ROOM) I-POD DOCKING STATION, WASHER / ...

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Property Type

Siesta Key Condo

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2 BR | 2 BA | Sleeps 6 | Quick View

6

$288

avg/night

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool
  • Rentals by owner

About this property

This colorful custom2rd floor unit has a commanding view of the Gulf of mexico.This special unit has been decorated by a pro, and shows it! unit, perfect for people who can take excellent care of things and appreciate the fine nature of this unit.From the modern kitchen, you will enjoy Siesta ...

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Property Type

Siesta Key Condo

"Wonderful Vacation"

This was a terrific place to stay with wonderful views of the gulf. It was a very pleasant and peaceful trip. Carrie was great to work with. Once she found out about a beach project date changing, she came ...

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3 BR | 2 BA | Sleeps 8 | Quick View

$267

avg/night

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Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool

About this property

CHARMING 3 BEDROOM PRIVATE HOME LOCATED IN THE QUIET SUB-DIVISION OF SIESTA ISLES. RELAX ON VACATION WITH ALL THE AMENITIES OF HOME. PRIVATE POOL, 2 CAR GARAGE, WASHER / DRYER, CHARCOAL GRILL, AND MUCH MORE. HOME OFFERS 2 LIVING ROOMS, ( ONE WITH LEATHER FURNITURE AND 53" T.V.), 6 T.V.'S, 2 ...

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Property Type

Siesta Key House

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool
  • Rentals by owner

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

"Wonderfully Relaxing"

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

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2 BR | 2 BA | Sleeps 4 | Quick View

Distance to beach: 800 feet to Siesta Key Beach

$159

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool
  • Rentals by owner

About this property

Brand New Condo, completely renovated. 2 Bedroom, 2 Bath large condo with granite kitchen and baths. Tile deck flooring. Full water views from our 6th floor location. See all the way to end of Anna Marie on clear day. Ringling bridge, downtown Sarasota, Lido and Bird Key views. King bed in master ...

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Property Type

Siesta Key Condo

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$750

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool
  • Rentals by owner

About this property

Create memories with friends and family at this unique, and spacious property only 10 minutes from Siesta Key Beach.. It is perfect for large groups or reunions as this house includes 3 separate living spaces and has a total of 13 beds. Right behind the main house, not only will you find a fun area to ...

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Property Type

Siesta Key Estate

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Studio | 1 BA | Sleeps 3 | Quick View

$143

avg/night

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Key Amenities

  • Air conditioning
  • Pool

About this property

GROUND FLOOR STUDIO LOCATED IN THE MIDDLE OF THE CASA MAR COMPLEX. SHORT DISTANCE FROM THE BEACH AND POOLS. UNIT OFFERS A BRAND NEW QUEEN MURPHY BED, 32" LCD FLAT SCREEN TV, DVD / VCR AND CD PLAYER. 1 COVERED PARKING SPACE. COMPLEX OFFERS 2 POOLS, TENNIS, SHUFFLE BOARD AND BEACH CHAIRS. COMPLEX ALSO ...

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Property Type

Siesta Key Condo

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

SIESTA BREAKERS - Siesta Key Beachfront Vacation Rental Condo on Crescent Beach (Two Bedroom Vacation Units for Rent)Located Directly on Crescent Beach on the middle of Siesta Key, Sarasota, FL BEAUTIFUL NEW LISTING: This beautiful, two bedroom, two bath, luxury Villa is located directly on the ...

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Property Type

Siesta Key Condo

"good place"

Comfortable and quiet at that time. I recommend it to everybody.. Please have more explanation to find the place to unlock the gate

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

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

"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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3 BR | 3 BA | Sleeps 6 | Quick View

8

Distance to beach: 0.3 miles to Crescent Beach

$356

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Rentals by owner

About this property

Welcome to your perfect vacation home on Siesta Key! Our turnkey townhouse is located just a few minutes' walk from the #1 ranked Crescent Beach, where you can enjoy the crystal-clear waters and powdery white sand that have made Siesta Key world famous.Our townhouse features a spacious courtyard ...

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Property Type

Siesta Key Townhome

"Paradise!"

The place was immaculate and had everything we needed. It was so nice to have beach towels, chairs, and sand toys provided. The location is perfect. It's a very short walk to the beach. Some restaurants ...

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1 BR | 1 BA | Sleeps 4 | Quick View

$112

avg/night

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Key Amenities

  • Air conditioning
  • Pool

About this property

COME RELAX IN THIS QUIET BAYSIDE COMPLEX THAT IS SURROUNDED BY WHISPERING OAKS. UNIT LOCATED ON THE 4TH FLOOR AND IS A 1 BEDROOM / 1 BATH CORNER UNIT. WASHER/DRYER IN UNIT. COMPLEX OFFERS POOL, TENNIS, 1 ASSIGNED COVERED PARKING SPACE. UNIT HAS 2 TV'S, DVD. HIGHSPEED INTERNET ACCESS, (SIESTA 4 RENT ...

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Property Type

Siesta Key Condo

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2 BR | 1 BA | Sleeps 6 | Quick View

10
last minute deal
LAST MINUTE DEAL 5/15 - 6/26: Siesta Key **Rarely open Summer dates -6/14 for 6 nights & 7/ 6-13. Private Villa steps to beach

$208

avg/night

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool
  • Rentals by owner

About this property

Our villa is located in Siesta Key, FL on Crescent (Siesta Key) Beach, FAMOUS for its powdery, sugar white sand and being VOTED #1 Beach in USA. The Beach has complimentary shade cabanas and beach chairsFeatures include 2 Bedrooms, 1Bath sleeping six with 1King and 2 queen beds. The kitchen is furnished ...

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Property Type

Siesta Key Villa

"Enjoyable VacationVilla"

The Villa was perfect for my December trip to Siesta Key! Very clean, appreciated lots of towels (which I find a plus staying other places they skimp on them), kitchen well equipped. Access to the beach ...

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DEAL

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool
  • Rentals by owner

About this property

A front row seat for the famous sands and sunsets of Siesta Key Step barefoot directly on to the award-winning, powdery sand of Crescent Beach Two of four bedrooms have gulf views Ideal for families or small groups of up to 8 people Enjoy access to an Olympic-sized pool Fully equipped kitchen Screened ...

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Property Type

Siesta Key House

"Perfect location! Wonderful accommodations!"

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

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$308

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

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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1 BR | 1 BA | Sleeps 4 | Quick View

$223

avg/night

View Details

Key Amenities

  • Air conditioning
  • Pool

About this property

1 BEDROOM, 1ST FLOOR CONDO W/ PRIVATE SCREENED LANAI, NEW PERGO FLOORS, NEW KITCHEN, WASHER/ DRYER IN UNIT. LOCATED ONLY 1 BLOCK FROM THE SHOPS AND RESTAURANTS IN THE VILLAGE, 1 BLOCK TO THE BEACH, SEPARATE DINING ROOM, HIGHSPEED INTERNET ACCESS, (SIESTA 4 RENT IS NOT RESPONSIBLE FOR TECH SUPPORT). POOL ...

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Property Type

Siesta Key Condo

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3 BR | 3 BA | Sleeps 8 | Quick View

$357

avg/night

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Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool

About this property

Tucked away amid the tropical tranquility of Siesta Keys Grand Canal, this totally remodeled modern style home delivers on design, location and lifestyle. Featuring three bedrooms and three baths and a one-car covered parking and laundry room with washer and dryer. Beautiful polished terazzo floors, open ...

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Property Type

Siesta Key House

Show less

Key Amenities

  • Air conditioning
  • Kitchen
  • Pool

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

"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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2 BR | 2 BA | Sleeps 6 | Quick View

$413

avg/night

View Details

Key Amenities

  • Air conditioning
  • Pool

About this property

***20% off stays in January 2024*** BEAUTIFUL BEACHFRONT CONDO WITH VIEWS FROM LIVING ROOM AND BOTH BEDROOMS. BEACH CHAIRS PROVIDED ON THE BEACH. LARGE LANAI RUNS ENTIRE WIDTH OF UNIT. LEATHER FURNITURE, ONE OF OUR MOST POPULAR UNITS. BIG SCREEN TV, VCRand DVD, TV IN EACH BEDROOM. WASHER and DRYER IN ...

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Property Type

Siesta Key Condo

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3 BR | 3 BA | Sleeps 6 | Quick View

$792

avg/night

View Details

Key Amenities

  • Air conditioning
  • Oceanfront
  • Pool

About this property

**Any advertised discounts on website do not apply to this unit*** Due to circumstances out of our control, the pool on the 2nd floor in between the buildings is closed due to refurbishment. You do still have the access to the pool that is on the beach. also the spiral staircase from this units balcony ...

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Property Type

Siesta Key Condo

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4 BR | 2.5 BA | Sleeps 10 | Quick View

$618

avg/night

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Key Amenities

  • Air conditioning
  • Private pool

About this property

Welcome to paradise! Your oasis awaits you. 4 bedrooms, 2.5 bath luxury townhome with a private pool is just 1 block from Siesta Village and only 2 blocks from the beach! Five star amenities include; Fully stocked gourmet kitchen with granite counter tops, top of the line stainless steel appliances, laundry ...

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Property Type

Siesta Key Condo

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3 BR | 3 BA | Sleeps 10 | Quick View

$267

avg/night

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Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool

About this property

COME RELAX IN THIS BEAUTIFUL 3 BEDROOM / 3 BATH UPDATED POOL HOME LOCATED IN A BEAUTIFUL SIESTA KEY NEIGHBORHOOD. HOME OFFERS NEW FURNISHINGS, GRANITE COUNTERTOPS, STAINLESS STEEL APPLIANCES, HIGH-SPEED INTERNET WITH BOOSTER, (SIESTA 4 RENT IS NOT RESPONSIBLE FOR TECH SUPPORT). ENJOY THE LARGE PRIVATE ...

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Property Type

Siesta Key House

Show less

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Pool
  • Rentals by owner

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

"What a Fantastic Little Gem!"

Siesta Key have become our favorite vacation spot and #409 at Crescent Royale was where my wife and I got to experience the very best thanks to Karen who accepted us in her beautiful and awesomely appointed ...

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2 BR | 2 BA | Sleeps 6 | Quick View

$310

avg/night

View Details

Key Amenities

  • Air conditioning
  • Oceanfront
  • Pool

About this property

GORGEOUS GULF FRONT, 2 BEDROOM / 2 BATH UNIT IN THE SOUGHT AFTER CRYSTAL SANDS COMPLEX. TILE FLOORS THROUGHOUT KITCHEN, BATHS and LIVING ROOM. 3 FLAT SCREEN T.V.'S, WASHER / DRYER AND SCREENED LANAI OFF ALL ROOMS WITH DIRECT ACCESS. HIGH SPEED WIRELESS INTERNET ALSO AVAILABLE, (SIESTA 4-RENT IS NOT ...

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Property Type

Siesta Key Condo

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4 BR | 2 BA | Sleeps 8 | Quick View

$407

avg/night

View Details

Key Amenities

  • Air conditioning
  • Private pool

About this property

A piece of Paradise..... Come relax in this beautiful 4 Bedroom, 2 full bath pool home offering large livingroom and family room, caged heated pool and spa, (spa is non-functional and is maintained at pool temperature.) 1 car garage ( owner keeps one car in garage), washer/dryer. Home located just 1 mile ...

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Property Type

Siesta Key House

Show less

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool
  • Rentals by owner

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

"Sisters beach retreat"

First of all Dina and Russ are wonderful hosts and made our stay in B106 very enjoyable. From the moment we walked in to the condo to hear light jazz playing on the TV’s, the mood was set for a relaxing ...

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1 BR | 1 BA | Sleeps 4 | Quick View

$197

avg/night

View Details

Key Amenities

  • Air conditioning
  • Pool

About this property

This adorable ground floor 1 bedroom unit in the Casa Mar complex on the beach side of Midnight Pass offers screened lanai overlooking courtyard with 2 pools, short distance down the sidewalk to the beach. Covered parking for 1 car. Tennisand Community laundry facilities. Beach chairs are provided by ...

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Property Type

Siesta Key Condo

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1 BR | 1 BA | Sleeps 4 | Quick View

$209

avg/night

View Details

Key Amenities

  • Air conditioning
  • Pool

About this property

This 1 bedroom is nestled in the middle of the Casa Mar complex on the Beach side of Midnight Pass, Offering ground floor, screened lanai overlooking courtyard with 2 pools, short distance down the sidewalk to the beach. Covered parking for 1 car. and tennis, Community laundry facilities. Beach chairs ...

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Property Type

Siesta Key Condo

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2 BR | 2 BA | Sleeps 6 | Quick View

$194

avg/night

View Details

Key Amenities

  • Air conditioning
  • Pool

About this property

Experience luxurious living in one of the largest units on Siesta at this stunning 2 bedroom, 2 bathroom condo. This immaculate condo features porcelain tile flooring in the living areas, brand new plush carpeting in both bedrooms, and beautiful crown molding throughout. The kitchen is a chef's dream, ...

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Property Type

Siesta Key Condo

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2 BR | 2 BA | Sleeps 6 | Quick View

3

Distance to beach: 0.1 miles to Crescent Beach Siesta Key

$170

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

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

"June Trip"

Check in was easy. Clean unit. Management staff were friendly and helpful. Beach area use could be more clear. The beach accessories were good.

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2 BR | 2 BA | Sleeps 6 | Quick View

1

$279

avg/night

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Private pool
  • Rentals by owner

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

"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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3 BR | 2 BA | Sleeps 8 | Quick View

$386

avg/night

View Details

Key Amenities

  • Air conditioning
  • Private pool

About this property

TRULY THE BEST OF BOTH WORLDS- BEAUTIFUL CANAL HOME JUST TWO BLOCKS TO WORLD-FAMOUS SIESTA KEY BEACH. COME RELAX IN THIS BEAUTIFUL 3 BEDROOM / 2 BATH HOME LOCATED IN THE QUIET NEIGHBORHOOD OF SIESTA ISLES WITH A GORGEOUS POOL. (NOTE POOL CAGE SHOWN IN SOME PHOTOS IS NO LONGER THERE.) THIS FABULOUS REMODELED ...

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Property Type

Siesta Key House

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

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

"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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2 BR | 2 BA | Sleeps 6 | Quick View

13

Distance to beach: 0.0 miles to Siesta Key Public Beach

$313

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool
  • Rentals by owner

About this property

This 2-bedroom, 2 bath Siesta Key condo can sleep 6 comfortably with a pull-out queen sofa bed and total square feet of 1,773! The beautifully decorated updated condo, with newly tiled bathrooms offers a comfortable, home-away-from-home feel. Sit on your private 20 ft deck and enjoy the view of a lake ...

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Property Type

Siesta Key Condo

"Siesta Key get away"

We loved the beautiful condo. It was our first trip to Siesta Key and we enjoyed it thoroughly. The condo was well kept, fully furnished for the most part and the Mgmt team was there to help us when we ...

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2 BR | 1.5 BA | Sleeps 6 | Quick View

$129

avg/night

View Details

Key Amenities

  • Pool

About this property

April 2024 rates have been lowered. ENJOY THIS SOUGHT AFTER GROUND FLOOR BAY VIEW UNIT WITH LARGE SCREENED LANAI OVERLOOKING THE CANAL. 2 TV'S W/DVD AND GORGEOUS POOL, TENNIS, WASHER DRYER IN UNIT. BEACH ACCESS RIGHT ACROSS THE STREET AND COVERED PARKING. UNIT OFFERS HIGHSPEED WI-FI INTERNET ACCESS, ...

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Property Type

Siesta Key Condo

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2 BR | 2 BA | Sleeps 6 | Quick View

$143

avg/night

View Details

Key Amenities

  • Air conditioning
  • Pool

About this property

2ND FLOOR UNIT, COMPLEX OFFERS, POOL, WIFI AT THE POOL AREA ONLY. ( SIESTA 4 RENT DOES NOT OFFER TECH SUPPORT), NEAR SHOPPING, 2 BLOCKS TO THE PUBLIC BEACH ACCESS, END UNIT OFFERS A LITTLE MORE SPACE. 2 WEEK MIN. LAUNDRY FACILITY ON 1ST FLOOR. 1 King, 2Twin, 1SOFA BED. CLEANING FEE $185

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Property Type

Siesta Key Condo

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2 BR | 2 BA | Sleeps 4 | Quick View

17

Distance to beach: 0.1 miles to Siesta Key Beach

$135

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Rentals by owner

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

"Amazing"

This rental property was perfect for our family!! It’s located directly across from the beach access and there are plenty of beach chairs, toys and umbrellas that are supplied. You can easily walk downtown ...

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2 BR | 1.5 BA | Sleeps 4 | Quick View

30
owner special
Owner special: End of July 22 through August is now available!

Distance to beach: 200 yards to Crescent Siesta Key Beach

$171

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool
  • Private pool
  • Rentals by owner

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

"Great Location!"

Love the location, close to beach and town! Walk to everything. The back patio was a plus!! I would recommend!

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3 BR | 2 BA | Sleeps 8 | Quick View

$280

avg/night

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Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool

About this property

CHARMING 3 BEDROOM / 2 BATH PRIVATE HOME LOCATED IN THE QUIET NEIGHBORHOOD OF ISLAND CIRCLE. APPROX. 2 BLOCKS FROM THE WORLD FAMOUS SIESTA BEACH AND APPROX. 1/2 MILE FROM SIESTA VILLAGE. HOME OFFERS A PRIVATE POOL *HEATED ( Nov- April only) , TILE FLOORING, 3 LCD TV’S, IPOD DOCKING STATION, WASHER ...

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Property Type

Siesta Key House

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2 BR | 2 BA | Sleeps 6 | Quick View

$166

avg/night

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Key Amenities

  • Air conditioning
  • Pool

About this property

4TH FLOOR BAYSIDE, 2 BEDROOM / 2 BATH CONDO LOCATED IN THE CAPRI BUILDING OF THE EXCELSIOR COMPLEX. THE COMPLEX HAS 2 POOLS (ONE ON BEACHSIDE AND ONE ON BAYSIDE) WITH HOT TUB, 3 LIGHTED TENNIS COURTS, OUTDOOR BARBECUE / PICNIC AREA AND BEACH ACCESS. UNIT OFFERS WASHER / DRYER, HIGH SPEED INTERNET SERVICE, ...

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Property Type

Siesta Key Condo

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2 BR | 2 BA | Sleeps 5 | Quick View

36
last minute deal
LAST MINUTE DEAL 5/25 - 6/8: Save over $1000/week May 25th - June 2nd or Save over $2400 for two weeks May 25th-June 8th

$494

avg/night

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool
  • Rentals by owner

About this property

The condo benefits from its own private pool. The living room, master bedroom, kitchen, and lanai (balcony) all have stunning ocean views. The lanai, with over $10,000 of new doors and windows, is furnished with a table and chairs to enable you to dine al fresco. There is also a beautiful couch to curl ...

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Property Type

Siesta Key Condo

"Fabulous Beachfront Siesta Key Condo"

We had a glorious week at Kevin and Elaine’s condo at Fisherman’s Cove. The location was perfectly private, steps to the beach. Condo was well appointed with everything we needed. Sunsets were to die ...

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DEAL

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

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

"GREAT!!"

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

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3 BR | 3 BA | Sleeps 6 | Quick View

3

$314

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool
  • Rentals by owner

About this property

Great house on Siesta key with pool and kanal. You can do fishing on the backside or have a jetski, boat there. Sometime you can see seacows on the kanal. 3 bedroom with 3 bath and a nice heated pool tp play in. Nice and quiet place it is, and so close to the Village and beach. Enjoy the place.

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Property Type

Siesta Key House

"Perfect Location"

Located close to the village and within walking distance of the beach. Plenty of room for families and amenities which included bikes for all ages. The pool is heated and such a great perk!

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1 BR | 1 BA | Sleeps 4 | Quick View

$112

avg/night

View Details

Key Amenities

  • Air conditioning
  • Pool

About this property

Beautiful 1 Bedroom w/ den in Bayside community of Bay Oaks. 3 TV's, 1st floor unit with new furnishings. Sleeps 4, King in the master bedoom. The den has a twin bed and the livingroom has a sleeper sofa. No cable, Streaming only. Highspeed internet. (SIESTA 4 RENT IS NOT RESPONSIBLE FOR TECH SUPPORT).1 ...

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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 238 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 $58 per night with an average price per night of $263.

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 59 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 53 oceanfront rentals in Siesta Key available on FloridaRentals.com. Use our filters to search and book yours today!