Siesta Key Vacation Rentals

(281 rentals)
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2 BR | 2.5 BA | Sleeps 6 | Quick View

$566

avg/night

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Key Amenities

  • Air conditioning
  • Pool

About this property

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** THIS 3RD FLOOR CONDO WAS RECENTLY REFURNISHED WITH ALL ROOMS GETTING ALL NEW FURNITURE AND FURNISHINGS AND ALL BEDS ...

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Property Type

Siesta Key Condo

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2 BR | 2 BA | Sleeps 6 | Quick View

$346

avg/night

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Key Amenities

  • Air conditioning
  • Pool

About this property

COME STAY AND RELAX IN THIS BEAUTIFUL 2 BEDROOM / 2 BATH CONDO LOCATED IN THE PALM BAY CLUB TOWER OVER-LOOKING THE WORLD FAMOUS SIESTA KEY BEACH, ( SAME SIZE AND VIEW AS PENTHOUSE UNIT.) ALL THE AMENITIES. FROM THE TILE FLOORING, GRANITE COUNTERTOPS AND STAINLESS STEEL APPLIANCES TO THE LEATHER FURNITURE, ...

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Property Type

Siesta Key Condo

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2 BR | 2 BA | Sleeps 6 | Quick View

$277

avg/night

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Key Amenities

  • Air conditioning
  • Pet friendly

About this property

1st Floor Duplex in the Siesta Village. This unit offers 2 Bedrooms, 2 Baths, tile floors, Leather furniture, screened lanai, washer/dryer in unit, pool shared with the 305 unit. Located in Siesta Village near all the restaurants and shops and about 2 blocks to Siesta Beach access. Unit offers high speed ...

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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

$207

avg/night

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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

5 BR | 3.5 BA | Sleeps 15 | Quick View

1

$787

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

73

Distance to beach: 0.0 feet to We are directly on the beach and direct oceanfront

$277

avg/night

View Details

Key Amenities

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

About this property

Our condo is directly on the beach and is direct oceanfront (Gulf-front). Unfortunately, there are properties on this site that falsely claim to be beachfront / oceanfront. We encourage travelers to ask property owners to verify those claims.When we travel over 1,000 miles to enjoy a beach vacation ...

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Property Type

Siesta Key Condo

"Paradise"

Our second year booking with Dina. Fabulous location (you won’t get any closer than this to the beach ) Condo was immaculate and beautifully decorated and was equipped with all the necessities, plus ...

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2 BR | 2 BA | Sleeps 6 | Quick View

$127

avg/night

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Key Amenities

  • Air conditioning
  • Pool

About this property

Welcome to our vacation oasis. We love the peaceful, friendly vibe of the Bay Oaks Community and hope you do as well. Our two bedroom, two bathroom second floor condo unit has been recently upgraded with new living and dining room furniture and new bedding in relaxed but upscale style. The complex sits ...

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Property Type

Siesta Key Condo

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2 BR | 2 BA | Sleeps 6 | Quick View

6

Distance to beach: 0.2 miles to Siesta Key

$202

avg/night

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Key Amenities

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

About this property

NEWLY REMODELED - LUXURY WATERVIEW CONDO FOR COUPLES or Families GETAWAY - POOLS, GYM, TENNIS - Walk to beach, town, shopping, top restaurants, live music, and entertainment.Walk out of the front door of this fantastic condo, grab your beach gear and take a short walk and you'll hit the beach ...

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Property Type

Siesta Key Condo

"Perfect gulf and bay Siesta Key condo"

This two bedroom Palm Bay Club condo has it all. It was exactly as described in the listing. We had everything we needed for a stress free comfortable stay. The beds were the most comfortable we have slept ...

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2 BR | 1.5 BA | Sleeps 5 | Quick View

Distance to beach: 250 feet to Siesta Key

$184

avg/night

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Key Amenities

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

About this property

On Siesta Key - Quick walk to Siesta Key's world famous beach. Beautiful and private, this updated condo with granite kitchen and tile floors overlooks the bay inlet and boat basin. Across street from world famous beach. Fully amenitied condo in amentied condo complex. Large community pool, tennis ...

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Property Type

Siesta Key Condo

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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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2 BR | 2 BA | Sleeps 6 | Quick View

$277

avg/night

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Key Amenities

  • Air conditioning
  • Pet friendly

About this property

2nd Floor, Duplex in Siesta Village. This unit offers 2 Bedrooms and 2 Baths, Shared pool with 303. washer/dryer in unit, screened lanai. Located near quaint shops and restaurants in Siesta Village and about 2 block to the Siesta Beach access. High speed internet- wifi ( Siesta 4 Rent does not offer tech ...

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Property Type

Siesta Key Condo

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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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Key Amenities

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

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

"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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4 BR | 2.5 BA | Sleeps 9 | Quick View

$295

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 remodeled home delivers on design, location and lifestyle. Featuring four bedrooms, two-and-one-half baths and a one-car garage and washer and dryer. Beautiful hardwood floors, solid wood cabinetry and sleek granite countertops. ...

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Property Type

Siesta Key House

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3 BR | 2 BA | Sleeps 10 | Quick View

$212

avg/night

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Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool

About this property

PRIVATE 3 BEDROOM / 2 BATH HOME LOCATED IN A BEAUTIFUL RESIDENTIAL NEIGHBORHOOD. 1 MILE FROM THE WORLD FAMOUS SIESTA KEY BEACH. FULLY RENOVATED AND NEWLY FURNISHED FOR YOUR ENJOYMENT WITH AN OPEN FLOOR PLAN WITH LOTS TO OFFER. KITCHEN W/ STAINLESS STEEL APPLIANCES AND LARGE PANTRY. 3 LCD SMART TVS, DVD. ...

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Property Type

Siesta Key House

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3 BR | 2.5 BA | Sleeps 8 | Quick View

$274

avg/night

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Key Amenities

  • Air conditioning
  • Pool

About this property

*** MARCH 2024 SPECIAL- NEW RESERVATIONS BOOKED AFTER 1/16/2024 $3500.00 A WEEK. Enjoy this 3 Bedroom 2.5 bath, Townhome in Midnight Cove 2 Complex. Complex has amenities galore, new rebuilt tennis courts, basketball, club house, fitness center, BBQ grilling area, heated pool and private docks. Offering ...

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Property Type

Siesta Key Condo

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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

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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2 BR | 2 BA | Sleeps 4 | Quick View

11

Distance to beach: 0.2 miles to Siesta Key Beach

$257

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Rentals by owner

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

"Gulf and Bay Bayside Unit #1344 D"

Lovely 2B/2B ground floor condo with fabulous sunroom getting morning sunshine. Sunroom faces a shell path that winds throughout the development and views lush landscape with blooming hibiscus bushes. Quiet ...

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1 BR | 1 BA | Sleeps 4 | Quick View

1

$143

avg/night

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Key Amenities

  • Air conditioning
  • Pool

About this property

This 1 bedroom , 2nd Floor unit in Siesta Village offers, great location 2 buildings from the beach, 1 block into the village with restaurants and shopping. The unit offers, central air, leather furniture, updated kitchen, 2 TV's. Complex offers community pool and laundry facilities located off common ...

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Property Type

Siesta Key Condo

"Siesta Key paradise"

We had a great vacation here! Condo was very nice, clean and well supplied. Close to Siesta Village, Beach and within walking distance of almost everything. A definite hidden treasure!

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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

$495

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

3 BR | 2 BA | Sleeps 8 | Quick View

$266

avg/night

View Details

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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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

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2 BR | 2 BA | Sleeps 6 | Quick View

4.6 rating on other travel sites

$285

avg/night

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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

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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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3 BR | 2 BA | Sleeps 8 | Quick View

1

$243

avg/night

View Details

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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2 BR | 2 BA | Sleeps 6 | Quick View

$305

avg/night

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Key Amenities

  • Air conditioning
  • Pool

About this property

Awesome 1st Floor Beachfront! Just outside your sliding doors is the #1 rated Crescent Beach. Condo features sweeping ocean view and super easy access to the beach while maintaining privacy of corner unit. Two bedrooms, two baths. Washer/dryer, Flat screen TVs in bedrooms 60" Ultra High Def 4k TV ...

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Property Type

Siesta Key Condo

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1 BR | 1 BA | Sleeps 4 | Quick View

2

$208

avg/night

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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 Rd. Ground floor unit, screened lanai overlooking courtyard with 2 pools, short distance down the sidewalk to the beach. Covered parking for 1 car, tennis, and community laundry facilities, NO SMOKING in ...

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Property Type

Siesta Key Condo

"Vintage Florida"

Fantastic spot! I would like to book the same time in 2024!Clean, well appointed, quiet. Beach is indescribably spectacular.

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2 BR | 2 BA | Sleeps 6 | Quick View

$309

avg/night

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Key Amenities

  • Air conditioning
  • Oceanfront
  • Private pool

About this property

BREATHTAKING GULF FRONT, 2 BEDROOM / 2 BATH UNIT IN THE BEAUTFUL CRYSTAL SANDS COMPLEX. GRANITE COUTERTOPS, TILE FLOORS IN KITCHEN, BATHS and LIVING ROOM, AND WOOD FLOORING IN BEDROOMS. LEATHER FURNITURE, 3 FLAT SCREEN T.V.'S, WASHER / DRYER AND SCREENED LANAI OFF ALL ROOMS WITH DIRECT ACCESS. HIGH ...

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Property Type

Siesta Key Condo

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3 BR | 3.5 BA | Sleeps 8 | Quick View

$266

avg/night

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Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool

About this property

ENJOY THIS 3 BEDROOM, 3 1/2 BATH UNIQUE PRIVATE HOME LOCATED ON TWO CANALS JUST EAST OF SIESTA VILLAGE. THE HOME WAS BUILT IN THE TRUE SARASOTA SCHOOL OF ARCHITECTURE DESIGN TO TAKE ADVANTAGE OF AIR FLOW AND LIGHT BUT ORIENTED SO THAT YOU NEVER HAVE DIRECT SUNLIGHT AT ANY TIME OF THE DAY. OPEN FLOOR PLAN ...

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Property Type

Siesta Key House

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Studio | 1 BA | Sleeps 3 | Quick View

$143

avg/night

View Details

Key Amenities

  • Pool

About this property

GROUND FLOOR STUDIO LOCATED IN THE MIDDLE OF THE CASA MAR COMPLEX. SHORT DISTANCE FROM THE BEACH AND ONE OF THE TWO POOLS IS DIRECTLY ACROSS THE UNIT. QUEEN MURPHY BED, 32 INCH FLAT SCREEN TV. 1 COVERED PARKING SPACE. COMPLEX OFFERS 2 POOLS, TENNIS, SHUFFLE BOARD AND BEACH CHAIRS. HIGH SPEED INTERNET ...

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Property Type

Siesta Key Condo

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4 BR | 3 BA | Sleeps 8 | Quick View

$346

avg/night

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Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool

About this property

ENJOY THIS 4 BEDROOM, 3 BATH PRIVATE HOME LOCATED ON A CANAL IN BEAUTIFUL SIESTA ISLES. OPEN FLOOR PLAN WITH LOTS OF SPACE, HARD WOOD FLOORS, A CAGED PRIVATE POOL WITH STUNNING VIEWS FROM EVERY ANGLE. LAUNDRY ROOM WITH FULL SIZE WASHER / DRYER AND WIRELESS INTERNET ACCESS, (SIESTA 4 RENT IS NOT RESPONSIBLE ...

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Property Type

Siesta Key House

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2 BR | 2 BA | Sleeps 6 | Quick View

$620

avg/night

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Key Amenities

  • Air conditioning
  • Pool

About this property

** 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** Luxury at its finest in this 1600 sq. ft. 2006 built Crescent condo complex. This Unique 2 Bedroom 2 Bath on the ...

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Property Type

Siesta Key Condo

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Studio | 1 BA | Sleeps 3 | Quick View

$143

avg/night

View Details

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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2 BR | 2 BA | Sleeps 6 | Quick View

$193

avg/night

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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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Key Amenities

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

About this property

Updated 2 bedroom unit in charming Casarina complex is located directly on the crystal white sands of Siesta Key Beach. Amenities galore! Magnificent gulf views. Enjoy the serenity of this casual, comfortable and tastefully decorated home away from home. You will enjoy having the In unit laundry, ...

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Property Type

Siesta Key Condo

"Lovely condo!"

This condo is lovely! It is spacious, with great sunset/beach views, beautifully and comfortably furnished, and very well equipped and supplied. Excellent location on Siesta Key - half way between both ...

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2 BR | 2 BA | Sleeps 6 | Quick View

$309

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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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

View Details

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

$386

avg/night

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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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2 BR | 2 BA | Sleeps 6 | Quick View

13

Distance to beach: 0.0 miles to Siesta Key Public Beach

$311

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 | 2 BA | Sleeps 6 | Quick View

$382

avg/night

View Details

Key Amenities

  • Air conditioning
  • Pool

About this property

Direct beachfront condo located on the desirable Crescent Beach at the southern end of Siesta Key. Views for miles of the sparkling Gulf of Mexico waters, white sand and Point of Rocks from all rooms. An open and spacious floor plan, generous balconies, washer and dryer in the condo. Covered parking, ...

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Property Type

Siesta Key Condo

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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3 BR | 3 BA | Sleeps 10 | Quick View

$266

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

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1 BR | 1 BA | Sleeps 4 | Quick View

$197

avg/night

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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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Key Amenities

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

About this property

This magnificent unit has been completely remodeled and is on the ground floor with beautiful water views and spectacular sunsets. Walk out the rear lanai door directly onto the beach where children can play within view or walk over the boardwalk to the blue-green waters of the Gulf of Mexico within 100 ...

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Property Type

Siesta Key Condo

"Paradise"

Our family spent the first week of April basking in the sun on Turtle Beach. We thoroughly enjoyed our week’s stay at this beautiful spacious 2 bedroom 2bath condo on the Gulf of Mexico. The condo was ...

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2 BR | 2 BA | Sleeps 7 | Quick View

Distance to beach: 0.0 miles to Siesta Key

$278

avg/night

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Pool

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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3 BR | 2.5 BA | Sleeps 6 | Quick View

2

Distance to beach: 1 miles to Turtle Beach

$146

avg/night

View Details

Key Amenities

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

About this property

This waterfront 3 bedroom Bungalow is nestled in an upscale area on Siesta Key between Turtle Beach (1 mi.), Crescent Beach (.5 mi.) and Siesta Key Beach (3 mi.) Free trolley can transport you to the beaches and restaurant in The Village. Enjoy your private dock on beautiful Heron Lagoon watching the ...

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Property Type

Siesta Key House

"Interior Designer"

The Bungalow is well designed as a beachy vibe...great location right on Midnight Pass. It is located at the quieter end of the key which we found more relaxing...great walking. The owners of the Bungalow ...

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2 BR | 2 BA | Sleeps 4 | Quick View

$152

avg/night

View Details

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

Show less

Key Amenities

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

About this property

March 2024 availability, won't last long, please contact us! This condo has not been a rental in the past, so you will not see reviews yet - but you can see our property management reviews on Florida Rentals #1258, #11647, #11646 & #11645! This vacation rental condo is directly on the beach ...

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Property Type

Siesta Key Condo

"Wonderfully located, fully equipped getaway!"

This condo was perfect for our vacation with my elderly mother. It was just a few steps from the beach and had everything we needed--quality beach chairs, umbrellas. Inside was well-appointed, too. Keurig ...

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen

About this property

VILLAGE WEST - Deluxe Ground Floor Vacation Condo in Siesta Key Village with Heated PoolLocated right in the Heart of Siesta Village, Sarasota FL - Short Walk to Crescent BeachVILLAGE WEST: This Siesta Key one bedroom ground floor condo vacation rental is located right in the heart of Siesta Village ...

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Property Type

Siesta Key Condo

"Great location!"

The location of this rental was perfect. We were able to walk into the village to shop and eat within a few minutes. Drive time to local attractions was minimal.

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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 281 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 $256.

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