Siesta Key Vacation Rentals

(226 rentals)
Tropical beach getaway at Sandy's Siesta Key Condo

2 BR | 1.5 BA | Sleeps 4 | Quick View

12

Distance to beach: 200 yards to Crescent Siesta Key Beach

$201

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • 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

"Wonderful Getaway"
Reviewed September 22, 2020

Sandy was amazing and so much help. She gave us great recommendations and we had an amazing time. It was a perfect getaway for our family.

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CocoBayou Cottage - Ask About $99 Down!

3 BR | 2 BA | Sleeps 10 | Quick View

Owner special: 10% off New Reservations the Holiday Week of December 19-26 (7 night minimum)!

$357

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool
  • Private Pool

About this property

This home could qualify for our BookCareFree promotion for 2020 and 2021 arrivals This includes: • Lenient Cancellation Policies • Deferred Payments • Adjusted Deposit Amounts Ask us about how you can qualify for this special offer!We go above and beyond the industry standard for ...

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Property Type

Siesta Key Cottage

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Siesta Key Beach direct access from your front door

$201

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool

About this property

Welcome to La Siesta Unit 112! This quiet 2-bedroom 2- full bath end unit is located on the ground floor of the La Siesta Condominiums complex with a direct walk out access to all Siesta Key Beach amenities. We are the closest home to the Sunset Pavilion, children's playground, and snack bar! Easily ...

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Property Type

Siesta Key Apartment

"Excellent"
Reviewed August 3, 2020

The condo was perfect! It had everything we needed for our vacation . The beds were very comfortable. The location was excellent close to the beach, which was right across the road . The pool was ...

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The Solaster - Ask About $99 Down!

6 BR | 6 BA | Sleeps 20 | Quick View

1
Owner special: 10% off New Reservations the Holiday Week of December 19-26 (7 night minimum)!

$635

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly
  • Private Pool

About this property

This home could qualify for our BookCareFree promotion for 2020 and 2021 arrivals This includes: • Lenient Cancellation Policies • Deferred Payments • Adjusted Deposit Amounts Ask us about how you can qualify for this special offer!We go above and beyond the industry standard for ...

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Property Type

Siesta Key House

"Great as advertised"
Reviewed October 31, 2019

A group of eight 80-ish college fraternity brothers got together for a reunion and rented Solaster. It was a great choice. The place is exactly as advertised: two attached units, six bedrooms with eight ...

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The Water is Great! Siesta Palms Sea Breeze #125

1 BR | 1 BA | Sleeps 4 | Quick View

Owner special: Autumn Special! Book 4 nights@$249/night+tax and get 1night Free. Complimentary bottle wine.

$245

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool
  • Rentals by Owner

About this property

Welcome to our Beach Get-away...where we invite you to relax, unwind and enjoy our casual Siesta Key way of life. The Siesta Palms by the Beach is just yards from the powdery-white sands of Siesta Key's world famous, award-winning Crescent Beach at Point of Rocks. With no streets to cross, it's 75 steps ...

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Property Type

Siesta Key House

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Coconut Grove - Ask About $99 Down!

6 BR | 6 BA | Sleeps 16 | Quick View

Owner special: 10% off New Reservations the Holiday Week of December 19-26 (7 night minimum)!

$626

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

This home could qualify for our BookCareFree promotion for 2020 and 2021 arrivals This includes: • Lenient Cancellation Policies • Deferred Payments • Adjusted Deposit Amounts Ask us about how you can qualify for this special offer!We go above and beyond the industry standard for ...

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Property Type

Siesta Key House

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Deluxe 2-BR Siesta Key Townhouse - Heated Pool - Siesta Key Village 2BR 5239

$265

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

SEASIDE VILLAS: This Siesta Key deluxe 2-Bedroom townhouse rental is located in the heart of Siesta Village – just steps to all the shops and restaurants and only a three minute walk to world famous Siesta Key Crescent Beach! Siesta Village has dozens of shops, fine or casual dining, pubs and clubs, ...

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Property Type

Siesta Key Townhome

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Sandy Seahorse Cottage - Ask About $99 Down!

6 BR | 6 BA | Sleeps 16 | Quick View

2
Owner special: 10% off New Reservations the Holiday Week of December 19-26 (7 night minimum)!

$532

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly
  • Pool
  • Private Pool

About this property

This home could qualify for our BookCareFree promotion for 2020 and 2021 arrivals This includes: • Lenient Cancellation Policies • Deferred Payments • Adjusted Deposit Amounts Ask us about how you can qualify for this special offer!We go above and beyond the industry standard for ...

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Property Type

Siesta Key House

"We had a excellent time!"
Reviewed August 20, 2020

Overall we had a very good time, everything was as we expected, except the BBQ that was very dirty and we had to clean it ourself.

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A special SECRET retreat...#26

1 BR | 1 BA | Sleeps 4 | Quick View

Distance to beach: 100 yards to Crescent Beach

$198

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Private Pool
  • Rentals by Owner

About this property

Simply relaxing one bedroom condo with a king bed facing the pool area and just a few steps to the private entrance to" Siesta Key #1 beach" white quartz sand beach . Additionally a Lazyboy queen Air Dream sofa sleeper for separate sleeping area if needed Unit includes a full kitchen for ...

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Property Type

Siesta Key Condo

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The Hummingbird - Ask About $99 Down!

6 BR | 6 BA | Sleeps 12 | Quick View

Owner special: 10% off New Reservations the Holiday Week of December 19-26 (7 night minimum)!

Distance to beach: 0.2 miles to Siesta Key Beach - Access # 5

$552

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool

About this property

This home could qualify for our BookCareFree promotion for 2020 and 2021 arrivals This includes: • Lenient Cancellation Policies • Deferred Payments • Adjusted Deposit Amounts Ask us about how you can qualify for this special offer!We go above and beyond the industry standard for ...

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Property Type

Siesta Key House

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Sea the View - Ask About $99 down!

4 BR | 3 BA | Sleeps 10 | Quick View

Owner special: 10% off New Reservations the Holiday Week of December 19-26 (7 night minimum)!

$528

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

This home could qualify for our BookCareFree promotion for 2020 and 2021 arrivals This includes: • Lenient Cancellation Policies • Deferred Payments • Adjusted Deposit Amounts Ask us about how you can qualify for this special offer!We go above and beyond the industry standard for ...

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Property Type

Siesta Key House

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Sophie's Quartier - Ask About $99 Down!

6 BR | 5 BA | Sleeps 16 | Quick View

Owner special: 10% off New Reservations the Holiday Week of December 19-26 (7 night minimum)!

$832

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

This home could qualify for our BookCareFree promotion for 2020 and 2021 arrivals This includes: • Lenient Cancellation Policies • Deferred Payments • Adjusted Deposit Amounts Ask us about how you can qualify for this special offer!We go above and beyond the industry standard for ...

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Property Type

Siesta Key House

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Caribbean Sol - Ask About $99 Down

5 BR | 5 BA | Sleeps 12 | Quick View

Owner special: 10% off New Reservations the Holiday Week of December 19-26 (7 night minimum)!

Distance to beach: 1 miles to Siesta Key Beach

$618

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Private Pool

About this property

This home could qualify for our BookCareFree promotion for 2020 and 2021 arrivals This includes: • Lenient Cancellation Policies • Deferred Payments • Adjusted Deposit Amounts Ask us about how you can qualify for this special offer!We go above and beyond the industry standard for ...

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Property Type

Siesta Key House

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Coral Breeze - Ask About $99 Down

3 BR | 2 BA | Sleeps 6 | Quick View

Owner special: 10% off New Reservations the Holiday Week of December 19-26 (7 night minimum)!

Distance to beach: 1 miles to Siesta Key Beach

$465

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool

About this property

This home could qualify for our BookCareFree promotion for 2020 and 2021 arrivals This includes: • Lenient Cancellation Policies • Deferred Payments • Adjusted Deposit Amounts Ask us about how you can qualify for this special offer!We go above and beyond the industry standard for ...

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Property Type

Siesta Key House

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Beautiful Renovated 2 Bedroom 2 Bath Waterview Condo, Pools, Tennis, Gym, Beach

2 BR | 2 BA | Sleeps 6 | Quick View

1

Distance to beach: 0.2 miles to Siesta Key

$254

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • 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

"The most beautiful and perfect get-a-way!"
Reviewed May 6, 2020

This condo was so beautiful! It was newly renovated and the decor was just stunning. The views were so incredible and the location was perfect. It is a very VERY short walk to the beach, which we loved. ...

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Luxurious Condo walk to Siesta Key Beach!

2 BR | 2 BA | Sleeps 4 | Quick View

2

Distance to beach: 0.5 miles to Siesta Key Beach

$150

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Rentals by Owner

About this property

Newly Renovated Vacation Rental on Siesta Key. Fully furnished, 2 bedroom/2 bathrooms in the prestigious Harbor Towers Yacht & Racket Club. Condo sleeps 4. King Bed in Master, 2 twin beds in second bedroom. New porcelain wood-look floors, new kitchen appliances, beautifully furnished, cable TV and ...

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Property Type

Siesta Key Condo

"Nice Condo"
Reviewed June 7, 2019

Nice clean condo, nice location (2 minutes drive from the free beach parking), nice gated complex with harbor view, pool, tennis courts.

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Turtle Beach - Gulf-Front Condo - 2BR - Free Boat Docks - Siesta Key 212B

$243

avg/night

View Details

Key Amenities

  • Air Conditioning

About this property

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 to the Gulf on all of Siesta Key. You could throw a tennis ball into the gulf from this Siesta Key beachfront condo! Located at Turtle Beach on ...

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Property Type

Siesta Key Condo

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Upscale 3-BR Siesta Key Townhouse - Heated Pool - Siesta Key Village 3BR 5241

$265

avg/night

View Details

Key Amenities

  • Air Conditioning

About this property

SEASIDE VILLAS: This Siesta Key deluxe 3-Bedroom townhouse rental is located in the heart of Siesta Village – just steps to all the shops and restaurants and only a three minute walk to world famous Siesta Key Crescent Beach! Siesta Village has dozens of shops, fine or casual dining, pubs and clubs, ...

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Property Type

Siesta Key Townhome

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Casita Lime - Ask About $99 Down!

2 BR | 2 BA | Sleeps 6 | Quick View

Owner special: 10% off New Reservations the Holiday Week of December 19-26 (7 night minimum)!

$252

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly
  • Private Pool

About this property

This home could qualify for our BookCareFree promotion for 2020 and 2021 arrivals This includes: • Lenient Cancellation Policies • Deferred Payments • Adjusted Deposit Amounts Ask us about how you can qualify for this special offer!We go above and beyond the industry standard for ...

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Property Type

Siesta Key House

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Sarasota-Siesta Key Coastal Five Bedroom with Pool and Spa

5 BR | 4 BA | Sleeps 13 | Quick View

3

Distance to beach: 400 feet to Siesta Beach

$591

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Private Pool

About this property

Excellent location at only 120 Yards To The Cool White Quartz Sand Of Siesta Beach! ?This Home Has Water Frontage on a Navigable Canal to the Bay And Then The Gulf of Mexico , Pool, Hot Tub And BBQ Area Within A Screen Enclosure. There Is A Nice Sized Sunning Patio As Well With Views Down The Waterway. ...

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Property Type

Siesta Key House

"Christmas Celebration"
Reviewed January 22, 2020

We, as a family of 12 celebrated our Christmas holiday at this location. It had everything one could think of. We have two sets of grandkids. The older ones were happy to have a hot tub, the little ones ...

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Vinca - Ask About $99 Down!

1 BR | 1 BA | Sleeps 2 | Quick View

Owner special: 10% off New Reservations the Holiday Week of December 19-26 (7 night minimum)!

Distance to beach: 0.2 miles to Siesta Key Beach - Access # 5

$98

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool

About this property

This home could qualify for our BookCareFree promotion for 2020 and 2021 arrivals This includes: • Lenient Cancellation Policies • Deferred Payments • Adjusted Deposit Amounts Ask us about how you can qualify for this special offer!We go above and beyond the industry standard for ...

View all property information

Property Type

Siesta Key Cottage

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Casita Coconut - Ask About $99 Down!

2 BR | 2 BA | Sleeps 6 | Quick View

Owner special: 10% off New Reservations the Holiday Week of December 19-26 (7 night minimum)!

$252

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly
  • Private Pool

About this property

This home could qualify for our BookCareFree promotion for 2020 and 2021 arrivals This includes: • Lenient Cancellation Policies • Deferred Payments • Adjusted Deposit Amounts Ask us about how you can qualify for this special offer!We go above and beyond the industry standard for ...

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Property Type

Siesta Key House

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Siesta Key Beach Front Ground Floor Condo104 Steps to the Beach WiFi

$286

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen

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

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Beach Time! - 2Br/2B Siesta Palms Sea Escape#225

2 BR | 2 BA | Sleeps 5 | Quick View

Owner special: Are you Dreaming of a White Christmas? Tranquil pool and spacious unit just steps to White Sand.

$350

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool
  • Rentals by Owner

About this property

Welcome to our Beach Get-away...where we invite you to relax, unwind and enjoy our casual Siesta Key way of life. The Siesta Palms by the Beach is just yards from the powdery-white sands of Siesta Key's world famous, award-winning Crescent Beach at Point of Rocks. With no streets to cross, it's 75 steps ...

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Property Type

Siesta Key Condo

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Siesta Dream House - Ask About $99 Down!

4 BR | 3.5 BA | Sleeps 12 | Quick View

Owner special: 10% off New Reservations the Holiday Week of December 19-26 (7 night minimum)!

$397

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Private Pool

About this property

This home could qualify for our BookCareFree promotion for 2020 and 2021 arrivals This includes: • Lenient Cancellation Policies • Deferred Payments • Adjusted Deposit Amounts Ask us about how you can qualify for this special offer!We go above and beyond the industry standard for ...

View all property information

Property Type

Siesta Key House

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Siesta Key - Gulf-Front Retreat - 2 BR – Free Boat Docks - Ground Floor 104B

$243

avg/night

View Details

Key Amenities

  • Air Conditioning

About this property

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 to the Gulf on all of Siesta Key. You could throw a tennis ball into the gulf from this Siesta Key beachfront condo! Located at Turtle Beach on ...

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Property Type

Siesta Key Condo

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The Grand Canal Cottage - Ask About $99 down!

5 BR | 4 BA | Sleeps 12 | Quick View

2
Owner special: 10% off New Reservations the Holiday Week of December 19-26 (7 night minimum)!

$596

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

This home could qualify for our BookCareFree promotion for 2020 and 2021 arrivals This includes: • Lenient Cancellation Policies • Deferred Payments • Adjusted Deposit Amounts Ask us about how you can qualify for this special offer!We go above and beyond the industry standard for ...

View all property information

Property Type

Siesta Key House

"Salt Life TWO THUMBS UP!"
Reviewed May 2, 2019

Location is literally right across a beach entrance a short 5min walk to the village. We rented both units and combined the common pool area for my whole extended family. It was fantastic!

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Honey Mango Cabana

2 BR | 1 BA | Sleeps 6 | Quick View

Owner special: 10% off New Reservations the Holiday Week of December 19-26 (7 night minimum)!

$226

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

Welcome to Honey Mango Cabana, one of Siesta Key’s most tropical beach bungalows with heated pool. When combined with its sister property Juicy Mango Cabana, both units make up Mango Manor.This tropical 2 bedroom/1 bathroom cottage is just a five minute walk to Crescent Beach and a short drive ...

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Property Type

Siesta Key House

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Casa De Siesta

4 BR | 3 BA | Sleeps 12 | Quick View

Owner special: 10% off New Reservations the Holiday Week of December 19-26 (7 night minimum)!

$446

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly
  • Private Pool

About this property

This uniquely configured vacation rental home is a combination of two units: “Villa Fiesta” and “Villa Margarita.” Each unit features their very own common spaces to include a living room, kitchen, dining area and a shared outdoor space. Casa De Fiesta is centrally located just ...

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Property Type

Siesta Key Villa

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Villa Margarita

2 BR | 2 BA | Sleeps 6 | Quick View

Owner special: 10% off New Reservations the Holiday Week of December 19-26 (7 night minimum)!

$223

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly
  • Private Pool

About this property

This uniquely configured vacation rental home is a combination of two units: “Villa Fiesta” and “Villa Margarita.” Each unit features their very own common spaces to include a living room, kitchen, dining area and a shared outdoor space. Casa De Fiesta is centrally located just ...

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Property Type

Siesta Key Villa

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SEA SHELL - Siesta Key Beach View Vacation Condo - 2 BR - on Crescent Beach

$217

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Beachfront

About this property

Sea Shell Condominium Complex: Located directly on world famous Crescent Beach this Siesta Key beachfront condo is right across the street from South Village with fast access on/off the island. This vacation condo is located in the Sea Shell Condominium Complex. Sea Shell is a smaller, more intimate, ...

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Property Type

Siesta Key Condo

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Siesta Key Luxury Condo 2/2, Pools, Tennis, Gym, walk to beach.

2 BR | 2 BA | Sleeps 6 | Quick View

5

Distance to beach: 0.4 miles to Siesta Key Main Beach, #1 in America!

$97

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Rentals by Owner

About this property

We are following strict CDC Guidelines for cleaning and sanitizing our condo before and after each Guest Stay. WE HAVE KEYLESS ENTRY ON BUILDING AND CONDO SO NO HUMAN CONTACT REQUIRED AT CHECK-IN OR DURING STAY.Resort like stay on Siesta Key in this spacious and bright 2 bedroom 2 bath condo. The ...

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Property Type

Siesta Key Condo

"COVID 19 TRIP TO SIESTA KEY"
Reviewed June 19, 2020

Sue is incredibly host. Easy to deal with and she is always there for you .Highly recommended! We would love to stay there again.

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Sol y Mar - Ask About $99 down!

4 BR | 2 BA | Sleeps 8 | Quick View

Owner special: 10% off New Reservations the Holiday Week of December 19-26 (7 night minimum)!

$426

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

This home could qualify for our BookCareFree promotion for 2020 and 2021 arrivals This includes: • Lenient Cancellation Policies • Deferred Payments • Adjusted Deposit Amounts Ask us about how you can qualify for this special offer!We go above and beyond the industry standard for ...

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Property Type

Siesta Key House

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La Casa Verde - Ask About $99 down!

4 BR | 2 BA | Sleeps 10 | Quick View

Owner special: 10% off New Reservations the Holiday Week of December 19-26 (7 night minimum)!

$596

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

This home could qualify for our BookCareFree promotion for 2020 and 2021 arrivals This includes: • Lenient Cancellation Policies • Deferred Payments • Adjusted Deposit Amounts Ask us about how you can qualify for this special offer!We go above and beyond the industry standard for ...

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Property Type

Siesta Key House

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Only on Siesta! Siesta Key Inn Majesty Palm #2C

2 BR | 1 BA | Sleeps 4 | Quick View

Owner special: Time to book your next Siesta Key Beach vacation! Comfy condo, Sunshine, blue skies, beach and pool.

Distance to beach: 150 yards to Siesta Key, Crescent Beach

$311

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool
  • Rentals by Owner

About this property

Welcome to our Beach Get-away...where we, The Koch Family, invite you to relax, unwind and enjoy our casual way of life. Resting just yards from the powdery-white sands of Siesta Key's world famous, award-winning Crescent Beach is our Family owned and operated Tropical Siesta Key Inn, it's a leisurely ...

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Property Type

Siesta Key Condo

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Tropical Resort-Like Oasis! 1 Br Siesta Palms Sea Spray #123

1 BR | 1 BA | Sleeps 4 | Quick View

Owner special: It's time to book your next Siesta Key Beach vacation! Fall Deal-Book 5 nights @ $235 and get 2 Free

$258

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool
  • Rentals by Owner

About this property

Welcome to our Beach Get-away...where we invite you to relax, unwind and enjoy our casual Siesta Key way of life. The Siesta Palms is just yards from the powdery-white sands of Siesta Key's world famous, award-winning Crescent Beach at Point of Rocks. With no streets to cross, it's 75 steps to the Gulf ...

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Property Type

Siesta Key Condo

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Pura Vida Oasis - Ask About $99 down!

5 BR | 3 BA | Sleeps 13 | Quick View

Owner special: 10% off New Reservations the Holiday Week of December 19-26 (7 night minimum)!

$742

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

This home could qualify for our BookCareFree promotion for 2020 and 2021 arrivals This includes: • Lenient Cancellation Policies • Deferred Payments • Adjusted Deposit Amounts Ask us about how you can qualify for this special offer!We go above and beyond the industry standard for ...

View all property information

Property Type

Siesta Key House

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The Nautilus - Ask About $99 Down!

8 BR | 6 BA | Sleeps 24 | Quick View

2
Owner special: 10% off New Reservations the Holiday Week of December 19-26 (7 night minimum)!

$999

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly
  • Private Pool

About this property

This home could qualify for our BookCareFree promotion for 2020 and 2021 arrivals This includes: • Lenient Cancellation Policies • Deferred Payments • Adjusted Deposit Amounts Ask us about how you can qualify for this special offer!We go above and beyond the industry standard for ...

View all property information

Property Type

Siesta Key House

"Beautiful Home"
Reviewed June 19, 2019

The Nautilus was a fantastic home on Siesta Key. Short walk to the beach and we had our own pool. House was well appointed and very comfortable and clean. We will be back and definitely recommend renting ...

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Tropical Escape! Fabulous Amenities 1Br Siesta Key Inn Coconut Palm #1C

1 BR | 1 BA | Sleeps 4 | Quick View

2
Owner special: Got Sunshine? Relax in our tropical oasis, tranquil pool and spacious unit just steps to beach.

$253

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Rentals by Owner

About this property

Welcome to our Beach Get-away...where we invite you to relax, unwind and enjoy our casual Siesta Key way of life. The Siesta Key Inn Siesta Palms is less than a block from the powdery-white sands of Siesta Key's world famous, award-winning Crescent Beach. We offer good "olde" fashioned Southern ...

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Property Type

Siesta Key House

"Nice place to relax in quiet surroundings"
Reviewed March 5, 2019

Perfect location to walk to beach ,bars , restaurants,a short drive over the bridge to Sarasota has all shopping you need. Very clean condo ,we met some very nice people that return every year.

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Siesta Key -2BR -Beachfront Condo on Crescent Beach -Heated Pool -Tennis Cts 515

$231

avg/night

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Key Amenities

  • Air Conditioning
  • Beachfront

About this property

BEAUTIFUL NEW LISTING: This beautiful, two bedroom, two bath, luxury Villa is located directly on the world famous Crescent Beach in the desirable Siesta Breakers Condo, notable for its resort-style amenities. Very stylish and contemporary in design with high end amenities inside and out. The exterior ...

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Property Type

Siesta Key Condo

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Fishermans Cove A102 - On Turtle Beach on Siesta Key

$246

avg/night

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Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Oceanfront
  • Pool
  • Rentals by Owner

About this property

My ground floor rental is directly on the beach on the Gulf of Mexico, with incredible views and sunsets!The lanai has a back door directly out to the Beach. The front of my unit faces the Lagoon where we have a FREE DOCK for your boat or other water craft. (So you have water views in both directions)! ...

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Property Type

Siesta Key Condo

"Heaven on Earth!"
Reviewed June 16, 2020

We stayed here to celebrate ten years together and it completely exceeded our expectations! The proximity to the beach (which is basically private) is unmatched and Carrie was so sweet and easy to work ...

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Couples and Family Friendly. Some pet friendly units are available too.

1 BR | 1 BA | Sleeps 4 | Quick View

2

Distance to beach: 20 yards to Siesta Key Beach

$207

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Pool
  • Private Pool

About this property

We are full turnkey condos. Our laundry facilities, gas grills around the pool, in unit cleaning supplies and dishwasher detergent are complementary. We are easily within walking distance to the Main Siesta Key beach (100 ft & across beach road to access #10) and the "Village"(most of the ...

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Property Type

Siesta Key Condo

"Great Plae to Stay!"
Reviewed February 19, 2020

we wanted a central location and a nice place to stay and we got both! Clean, welcoming, staff was great. Free trolley right up the road and beach is a 3 minute walk. The pool was great, even a hot tub! ...

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Crescent Cottage - Ask About $99 Down!

4 BR | 3 BA | Sleeps 10 | Quick View

Owner special: 10% off New Reservations the Holiday Week of December 19-26 (7 night minimum)!

$423

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly
  • Private Pool

About this property

This home could qualify for our BookCareFree promotion for 2020 and 2021 arrivals This includes: • Lenient Cancellation Policies • Deferred Payments • Adjusted Deposit Amounts Ask us about how you can qualify for this special offer!We go above and beyond the industry standard for ...

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Property Type

Siesta Key House

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Beachfront Siesta Key, FL.- 3 Bedroom Private Home W/Full Gulf Views!

3 BR | 3 BA | Sleeps 7 | Quick View

4

Distance to beach: 300 feet to Siesta Beach

$635

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Kid Friendly
  • Oceanfront
  • Pet Friendly
  • Rentals by Owner

About this property

This home has private Siesta Key beach frontage on the prime section of beach, there are no streets to cross or homes between you and the beach. Nearly every room has a full view of the beach and Gulf of Mexico. The entire back of this house opens with stacking glass sliding doors to catch the Gulf breezes ...

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Property Type

Siesta Key House

"Relaxation and BEAUTIFUL Beach!"
Reviewed September 3, 2020

Great beachfront home! David was a wonderful host! The beach is BEAUTIFUL!! Fluffy white sand and clear blue water! Such a relaxing vacation. The house is very close to the Siesta Key Village full of restaurants ...

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The Sun Dial - Ask About $99 Down!

4 BR | 4 BA | Sleeps 12 | Quick View

1
Owner special: 10% off New Reservations the Holiday Week of December 19-26 (7 night minimum)!

$670

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

This home could qualify for our BookCareFree promotion for 2020 and 2021 arrivals This includes: • Lenient Cancellation Policies • Deferred Payments • Adjusted Deposit Amounts Ask us about how you can qualify for this special offer!We go above and beyond the industry standard for ...

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Property Type

Siesta Key House

"Best Vacation yet!"
Reviewed July 20, 2020

We absolutely loved staying here! It was so quiet and relaxing, we couldn't have asked for anything more. We enjoyed the pool, beaches, local ice cream and especially the view. We can't wait to go back!

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Siesta Key Beachfront Condo with Gulf View!

$187

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Kid Friendly
  • 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

"Beautiful view of a world-class beach!"
Reviewed November 16, 2018

The tidy condo was well located on the 4th floor allowing for a magnificent view of the beach from the lanai. Great place to take our coffee in the morning before our morning walk; or a glass of wine in ...

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Ocean’s Edge - Ask About $99 down!

4 BR | 4 BA | Sleeps 8 | Quick View

Owner special: 10% off New Reservations the Holiday Week of December 19-26 (7 night minimum)!

$670

avg/night

View Details

Key Amenities

  • Pool
  • Private Pool

About this property

This home could qualify for our BookCareFree promotion for 2020 and 2021 arrivals This includes: • Lenient Cancellation Policies • Deferred Payments • Adjusted Deposit Amounts Ask us about how you can qualify for this special offer!We go above and beyond the industry standard for ...

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Property Type

Siesta Key Condo

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Blu Sky Cottage – Ask About $99 down!

3 BR | 2 BA | Sleeps 10 | Quick View

Owner special: 10% off New Reservations the Holiday Week of December 19-26 (7 night minimum)!

$494

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

This home could qualify for our BookCareFree promotion for 2020 and 2021 arrivals This includes: • Lenient Cancellation Policies • Deferred Payments • Adjusted Deposit Amounts Ask us about how you can qualify for this special offer!We go above and beyond the industry standard for ...

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Property Type

Siesta Key Cottage

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Siesta Key Condos - Gulf & Bay Club Bayside Condo

1 BR | 1 BA | Sleeps 2 | Quick View

1
Owner special: Contact owner for deals.

$164

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full 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

"Fabulous"
Reviewed September 7, 2019

A beautiful complex with a beach house feel ! A very welcoming unit with a generous space. Making the best of the intercostal and gulf !

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Honeysuckle - Ask About $99 Down!

3 BR | 3 BA | Sleeps 6 | Quick View

Owner special: 10% off New Reservations the Holiday Week of December 19-26 (7 night minimum)!

$276

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool

About this property

This home could qualify for our BookCareFree promotion for 2020 and 2021 arrivals This includes: • Lenient Cancellation Policies • Deferred Payments • Adjusted Deposit Amounts Ask us about how you can qualify for this special offer!We go above and beyond the industry standard for ...

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Property Type

Siesta Key House

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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°

Siesta Key condo rentals in gulf coast Florida's top barrier island

Siesta Key is a barrier island in the Gulf of Mexico, off the coast of Sarasota, Florida. It’s known for its sandy beaches and friendly locals. Fine white sand and gentle gulf breezes keep visitors coming back year after year. An ideal escape for a couple looking for romance, or a family looking to escape the Disney or Panama City crowds.

Siesta Key has amazing beach front with available rentals for you. When staying in one of our Siesta Key vacation rentals instead of hotel, you’ll have much more space and privacy, plus cost savings when booking a property for a large group. Use the filters to narrow down your choices and choose the rental that calls to you.

Climate

Prevalent sunshine and gentle coastal breezes should be expected daily. Sounds incredible, right? Well, it is. With well over 300 sunny days per year, you’d be hard pressed to visit Siesta Key at a “bad time”. Low humidity makes the area comfortable, as well as warm. Bring your sunblock to protect against UV rays and don’t forget a few pairs of swim trunks, as the warm gulf waters are perfect for boogie boarding and bodysurfing.

Getting around

From November to September the Siesta Key Trolley will take you from the southernmost part of the island to the north end. The 3 open air trolleys run 7 days a week from 8-Midnight between Turtle Beach to Siesta Village. They will pass by about every 20-30 minutes. So don’t worry too much about getting around this small barrier island. Plus, bike or scooter rentals are everywhere -- so you can exercise while you move from beach to beach.

For those who drive, two bridges link the island to the mainland. The north bridge, Siesta Drive, is within the City of Sarasota and provides convenient access to the city, its business and arts districts, and to the Sarasota/Bradenton International Airport via US Highway 41. The south bridge, Stickney Point Road, provides access to south Sarasota County and a direct route to Interstate 75.

Top activities and attractions

Let’s be serious: you’re visiting Siesta Key for the pristine beaches along the 35 miles of coastline. Here are the names to remember: Siesta Beach, Turtle Beach, and Crescent Beach. Each features soft quartz sand and warm gulf seas. The sand is cool on your feet, so you can take an extended walk by the ocean without fear.

Siesta Beach has relatively shallow waters and it is monitored by lifeguards year-round. Plus, there’s plenty of room to spread out and enjoy a long, relaxing day. Turtle Beach is the most active (think volleyball net and horseshoe pits) while Crescent Beach is known for its seclusion and relaxed atmosphere.

Just off the southern tip of Crescent Beach is Point of Rocks, one of the best places for snorkeling and underwater exploration along the Gulf Coast beaches. It is made up of large chunks of limestone covered with coral and sponges and a range of sea life inhabit these underwater formations.

Bring your clubs here, too. With over 100 golf courses in the area you’ll want to take advantage of the sunny days out on the links. There’s ample opportunity for water sports for those who shun dry land. Visitors can find companies offering kayaking, paddle boarding, deep sea fishing and much more.

Just north of Siesta Beach, Siesta Key Village has many stores ranging from hip and funky to high-end boutiques and, of course, we wouldn't be a beach town without the beach accessory and souvenir shops.

Events 

If you love carefully constructed creations, visit in May for the sand castle competition. Local sand artisans and amateurs try their hand at creating jaw-dropping scenery out of sand.

Every Sunday there’s the Drum Circle featuring a cacophony of sound from various instruments performed by locals and tourists. Enjoy a stroll through the galleries of Palm Avenue on the first Friday of every month. In addition to fine galleries, this area along lower Main Street is known for its unique variety of shops and restaurants.

In April, the aptly named Siesta Fiesta takes place. Stroll along the beach while enjoying fine art and handmade crafts from 200 of the nation’s most talented artists and crafters. Showcasing an extensive collection of work ranging from life-size sculptures, spectacular paintings, one-of-a-kind jewels, photography, ceramics and more, this show truly has something for anyone. Complete with an additional green market, this spectacular show also features plants, body products, and tasty dips.

Siesta Key house rentals on FloridaRentals.com

Booking a condo for rent in Siesta Key on FloridaRentals.com can save you up to 20% over our competitors. Plus, we have a wide array of inventory appealing to any group size or traveler tastes. Happy planning!