Siesta Key Vacation Rentals

(203 rentals)
Siesta Dream House

4 BR | 3.5 BA | Sleeps 12 | Quick View

$254

per night

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Key Amenities

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

About this property

Welcome to the Siesta Dream House!Hidden within Siesta Key lies a luxurious villa in all of it's splendor. Just after you cross the North Bridge from the mainland in the coveted northern part of the Island, among some of Siesta’s wealthiest homes, lies the charming "Siesta Dream House." ...

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Property Type

Siesta Key House

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Sophie’s Quartier

6 BR | 5 BA | Sleeps 16 | Quick View

$594

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Welcome to Sophie’s Quartier, a waterfront compound consisting of two homes right near Siesta Key Beach! This is a perfect retreat for huge family and friends’ get togethers! Enjoy a heated pool, one hot tub, two docks overlooking The Grand Canal of Siesta Key. Minutes walk from the world ...

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Property Type

Siesta Key House

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La Casa Verde

4 BR | 2 BA | Sleeps 10 | Quick View

$440

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

The waterfront cottage, ‘La Casa Verde’ is a very luxurious and large four [4] bedroom canal front heated pool home with two very large bathrooms in approximately 2,800 square feet of air conditioned living space. As you approach the home you are immediately drawn into it by volumes of lush, ...

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Property Type

Siesta Key House

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Casa Ohana

4 BR | 3 BA | Sleeps 12 | Quick View

1

$288

per night

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Key Amenities

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

About this property

Welcome to Casa Ohana! Our newly constructed luxury cottage (completion date of June 2017) has all the amenities your large group [up to 12!!!] can fathom. The location is THE premier location in the heart of Siesta Key Village, just behind Gilligan's and Lelu's Coffee Shop! Inside you’ll enjoy ...

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Property Type

Siesta Key House

"Great Family Vacation"
Reviewed March 1, 2018

The condo was great for our three generation family including a 3 year old and an infant. Private pool + easy walk to beach and restaurants met our needs. No parking issues to worry about. The Cottages ...

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Adorable Condo -- On Beach and Bay, 2 Bdr. Ground Floor

2 BR | 1 BA | Sleeps 4 | Quick View

Distance to beach: 0.2 miles to Siesta Key Beach

$136

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool

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. The complex is a gated resort community featuring unique “Old Key West style” condominiums only a ...

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Property Type

Siesta Key Condo

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"Menorca" 378 Canal Rd.

Studio | 1 BA | Sleeps 2 | Quick View

1

$81

per night

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Key Amenities

  • Air Conditioning
  • Private Pool

About this property

Studio/Efficiency, Queen Bed, Next to pool. Pool Access, WIFI *W&D access, ground floor. Local free shuttles so no need for a car.Located on the Voted number “#1 Beach in America” popular Siesta Key in Sarasota, Florida, the perfect vacation getaway.The unit maintains that great ...

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Property Type

Siesta Key Studio

"Small but everything!"
Reviewed March 28, 2019

I loved the pool, I was only one using it most of the time. Clean and warm, salt water. The bedroom was small, but it was a studio apartment, plenty of storage in armoire. Bed was softer and comfy. ...

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Luxury Siesta Key 4 bedroom Waterfront Home Only 5 minutes walk to Siesta Beach!

4 BR | 4.5 BA | Sleeps 12 | Quick View

2

Distance to beach: 120 yards to Siesta Beach

$595

per night

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Key Amenities

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

About this property

This Luxury Four Bedroom, Four and a Half Bathroom Home will leave you breathless as you enter. There are not many large rental homes, this close to Siesta Beach, that live like this home. Most Rentals by the beach have their living area 16 feet above the ground level and the pool below, which is not ...

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Property Type

Siesta Key House

"Spring Break 2019"
Reviewed April 1, 2019

The pictures do not do justice what an awesome place to stay. My family loved staying at this home David Butler Owner Agent (first class treatment) very impressed I would give this place a 5-Star x10

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Sandy Seahorse Cottage

6 BR | 6 BA | Sleeps 16 | Quick View

$359

per night

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Key Amenities

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

About this property

Welcome to the Sandy Seahorse Cottage!This uniquely configured private home [Sandy Cabana and Seahorse Cabana] is the perfect escape for you and your family and friends. This gorgeous beachy getaway comfortably sleeps 12 with a little room for more! The property has recently been updated with new ...

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Property Type

Siesta Key House

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Sea la Vie – 5321 (R)

3 BR | 2 BA | Sleeps 8 | Quick View

$214

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Welcome to Sea la Vie! This private 3BR/2BA home is the perfect beach getaway to relax, unwind & take in everything Siesta Key has to offer. The best part? The Salt Life is just 1 minute (seriously!) away from Siesta Key Beach, voted the # 1 beach in the U.S! Sea la Vie offers a shared heated pool ...

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Property Type

Siesta Key House

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Isla Amor – Stunning 5 BR/3BA Heated Pool Home on The Grand Canal

$604

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Welcome to Isla Amor. An absolute one of kind, limited edition home located in the "heart of the Siesta Key" on the prestigous Palm Island (the island within the island). Featuring a private heated pool, near America's #1 Beach, on the Grand Canal with intracoastal bay access and a boat dock. ...

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Property Type

Siesta Key House

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Casa Tegula

4 BR | 3 BA | Sleeps 12 | Quick View

$257

per night

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Key Amenities

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

About this property

Welcome to Casa Tegula! Our newest south Siesta Key luxury cottage has all the amenities your large group - up to 12. Enjoy a private heated pool & nearby beach access. When reserved with Casa Stolida to become The Nautilus, you can sleep up to 24. Welcome to Casa Tegula! Our newly constructed luxury ...

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Property Type

Siesta Key House

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"Key West" 378 Canal Rd.

2 BR | 2 BA | Sleeps 6 | Quick View

Owner special: Off season special! 20% discount May 18- 25.

$151

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly

About this property

2 BEDROOM/2 bath, Large Deluxe unit, King bed, Queen bed and Queen sleeper sofa, 3 TVs, large deck with awning, small screened porch, an upstairs accommodation. Pool Access, WIFI, private W&D, an upstairs accommodation. Local free shuttles so no need for a car.Located on the Voted number “#1 ...

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Property Type

Siesta Key House

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The Palms Cottage

4 BR | 2 BA | Sleeps 10 | Quick View

$385

per night

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Key Amenities

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

About this property

Welcome to The Palms Cottages! A gorgeous 4 bed/2 bath Siesta Key vacation home with heated pool, spa, covered lanai and views of the canal. Tropical landscape with large trees, mangroves & sea grapes. Walking distance to beach and Siesta Village! Welcome to the recently renovated Palms Cottage, ...

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Property Type

Siesta Key House

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Casa Stolida

4 BR | 3 BA | Sleeps 8 | Quick View

$257

per night

View Details

Key Amenities

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

About this property

Welcome to Casa Stolida! Our newest south Siesta Key luxury cottage has all the amenities your large group - up to 12. Enjoy a private heated pool & nearby beach access. When reserved with Casa Tegula to become The Nautilus, you can sleep up to 24. Welcome to Casa Stolida! Our newly constructed luxury ...

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Property Type

Siesta Key House

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

1 BR | 1 BA | Sleeps 4 | Quick View

Distance to beach: 20 yards to Siesta Key Beach

$171

per night

View Details

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

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2BR2BA 2nd Floor 800sqft Condo Siesta Key Crescent Beach + WiFi No Road to Cross

2 BR | 2 BA | Sleeps 7 | Quick View

2

Distance to beach: 120 yards to Siesta Key Crescent Beach

$100

per night

View Details

Key Amenities

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

About this property

Dr. Beach names Siesta Beach Best Beach in US - just Google 'dr beach names siesta beach best beach in us' and find out why. We have a new 360 degree picture layout of all rooms, similar to Real Estate Salesman version. Email us for a link. ... (If Available) Last Minute Discount: Save $200/wk Book ...

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Property Type

Siesta Key Condo

"T&P W."
Reviewed February 16, 2019

This rental was very nice. It more than met our expectations. We would not hesitate to rent from this gentleman again. He was very quick in his response to our initial reservation and followed up with us ...

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Dolphin" 378 Canal Rd. Just a short walk to the beach and Village

1 BR | 1 BA | Sleeps 4 | Quick View

Owner special: Off season special! 20% discount May 18- June 1.

$103

per night

View Details

Key Amenities

  • Air Conditioning
  • Kid Friendly
  • Pool

About this property

1 Bedroom, King Bed & Queen Sleeper, Ground level, Screen Porch. Pool Access, WIFI *W&D access, and ground floor. Across from Canal

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Property Type

Siesta Key Apartment

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BEAUTY AT THE BEACH--Full front Gulf view!! Crescent Arms 601S

$214

per night

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Key Amenities

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

About this property

THE BEACH IS CALLING AND I MUST GO!! *We invite you to come stay with us in the Crescent Arms South Tower--Condo 601S--directly on the #1 famous Crescent Beach with a FULL view of the Gulf on a private 32 foot lanai.*Decorated in a "beachy motif" with granite counter tips in the kitchen ...

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Property Type

Siesta Key Condo

"Beautiful beach and condo!!"
Reviewed July 25, 2018

The beach and condo were perfect. The sand was so soft and cool. The condo was decorated beautifully. There were 4 people staying in the condo and it had enough room for a couple more. We will be returning ...

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*Fantastic Bay View Condo* Siesta Key #1 Beach of the US

2 BR | 1.5 BA | Sleeps 4 | Quick View

LAST MINUTE DEAL 4/14 - 5/26: BOOK NOW Special Rate for April 23-30, 2019 *** We have water temperatures of 76 F in the gulf ****

$125

per night

View Details

Key Amenities

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

About this property

Vacation rental with private beach on the # 1 beach in the USA - Siesta Key on the Gulf of Mexico (Sarasota)Siesta Key, awarded for its pristine, powdery white beaches and its azur blue waters is the perfect escape from everyday life.Whether you are looking for a perfect destination for your vacation, ...

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Property Type

Siesta Key Apartment

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DEAL
Latitude Adjustment

4 BR | 4 BA | Sleeps 10 | Quick View

$294

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Welcome to Latitude Adjustment! This breathtaking 4 bedroom, 4 bathroom home is perfectly situated between America's #1 beach in the world and Siesta Key's famous North Village! You will not be able to ask for more as you drive up to this tropical oasis, covered with vibrant hot pink bougainvillea flower ...

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Property Type

Siesta Key House

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Beautiful Siesta Key Beach Condo-GREAT LOCATION! 3 Min WALK to Beach!

$159

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool

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 condo, with two updated, 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

"Perfect Honeymoon Getaway!"
Reviewed July 30, 2018

We stayed at this condo for 12 days for our honeymoon in June. The location of the condo is perfect with the public beach access right across the street (no need to drive to get to the beach) and just a ...

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Fishermans Cove A102 - On Turtle Beach on Siesta Key

$164

per 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

"My Home away from home"
Reviewed June 12, 2018

The condo is very clean and has everything you need for your vacation.The view is spectacular and the sunsets are magnificent, people will come from all over just to see them.This is why I call it my home ...

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Modernized Direct Waterfront Condo 2BR, 2B,HDTV, WIFI, Washer/Dryer, Gulf Lanai

$164

per night

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Key Amenities

  • Air Conditioning
  • Beachfront
  • Full 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

"good"
Reviewed August 19, 2018

we have the time ok but the red tide not let us have good time

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Overlooking Beach and one block to Siesta Village - Starfish unit

$250

per night

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Key Amenities

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

About this property

Beautiful, beach front apartments on Siesta Key. One bedroom, one bathroom, all linens, full size modern kitchen, living room with queen size sleeper couch, flat screen tvs in the living room and bedroom with Verizon Fios, and free wi-fi. French doors open onto your own private deck with patio furniture ...

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Property Type

Siesta Key Apartment

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Siesta Salt Life

6 BR | 4 BA | Sleeps 16 | Quick View

$404

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Welcome to The Salt Life! This private 6BR/4BA home is a unique combination of two units: “Sea Esta” & “Sea La Vie” (2328 sq. ft. total). Each unit features a 3BR/2BA configuration, each with their very own common space to include a kitchen, dining area, and private outdoor ...

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Property Type

Siesta Key House

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The Big Kahuna

8 BR | 6 BA | Sleeps 24 | Quick View

$577

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Welcome to The Big Kahuna! Our newly constructed luxury cottage (completion date of June 2017) has all the amenities your large group [up to 24!!!] can fathom. It also boasts the very BEST location, in the heart of Siesta Key Village, just behind Gilligan's and Lelu's Coffee Shop! Inside you’ll ...

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Property Type

Siesta Key House

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Siesta Key Beach Private Pool Home

$286

per night

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Key Amenities

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

About this property

Single family home with private heated caged pool. Large open floor plan in living area to kitchen and enclosed pool and deck. 3 bedrooms, 2 of which are master suites with ensuite full baths, flat screen TV's, king beds, and sliding glass doors to either caged pool deck or open air sundeck. 3rd bedroom ...

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Property Type

Siesta Key House

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The Seagull – 2/2 Condo with Heated Shared Pool in Heart of Siesta Key Village

$176

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool
  • Private Pool

About this property

Welcome to The Seagull, a 2BD/2BA private condo perfectly located only 1/2 mile from Siesta Beach and located in the heart of Siesta Key Village. This spaciously designed open floorplan comfortably sleeps 8! JUST WAIT TO SEE IT! NEWLY UPDATED FURNITURE AND UPDATED PHOTOS TO FOLLOW ON 6/29! The Seagull ...

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Property Type

Siesta Key Condo

"Siesta Key"
Reviewed October 23, 2018

Super place and had easy access to the Village.....would go back for sure!

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The Canopy Cottage

4 BR | 3 BA | Sleeps 9 | Quick View

$330

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

Welcome to The Canopy Cottage! Nestled deeply into a beautiful neighborhood canopied by Florida's oldest trees, this lovely 4/3 home that sleeps 9 features a heated pool/spa under a screened in lanai just a few minutes from America's #1 Beach! Welcome to The Canopy Cottage! Nestled deep into a beautifully ...

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Property Type

Siesta Key Cottage

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The Pearl by the Sea

4 BR | 3 BA | Sleeps 12 | Quick View

$550

per night

View Details

Key Amenities

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

About this property

Welcome to The Pearl by the Sea. An absolute one of kind, limited edition home located on prestigous Siesta Key featuring a private heated pool and spa, near America's #1 Beach, on the Grand Canal with intracoastal bay access and a boat dock. You have arrived...If you have ever gone searching for ...

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Property Type

Siesta Key House

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Fishermans Cove A302

2 BR | 2 BA | Sleeps 6 | Quick View

3

$164

per night

View Details

Key Amenities

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

About this property

This colorful custom 3rd floor unit has a commanding view of the Gulf of mexico.This special unit has been decorated by a pro, and shows it! This is an adults only unit, perfect for a mature couple who can take excellent care of things and appreciate the fine nature of this unit.From the modern ...

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Property Type

Siesta Key Condo

"Paradise at Christmas!"
Reviewed January 8, 2019

My family of four traveled to Siesta Key for Christmas week and enjoyed this precious condo on the beach! It was delightful! Fun colorful décor, comfortable, and all amenities included. The Sunset here ...

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Sol y Mar

4 BR | 2 BA | Sleeps 8 | Quick View

$287

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Welcome to Sol y Mar! A uniquely configured South Siesta Key private home with 4 bedrooms, 2 bathrooms that sleeps 8. May also be used as 2 separate units surrounded by lush gardens with a private beach access, a heated swimming pool and hot tub. Welcome to Sol y Mar. This COMPLETELY RENOVATED, single ...

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Property Type

Siesta Key House

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West Shore - 4BR/4.5BA Beach Front Condo, Heated Pool, With Private Beach Access

$550

per night

View Details

Key Amenities

  • Pool
  • Private Pool

About this property

Welcome to West Shore! A massive gulf front penthouse located right on Siesta Beach in a newly constructed building. With amazing views, a heated pool, and enough room to sleep up to 8, it is the only way to experience Siesta Key!West Shore is a luxuriously appointed penthouse in an extremely private ...

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Property Type

Siesta Key Condo

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Ocean’s Edge- 4BR/4.5BA Beachfront Condo, Heated Pool, With Private Beach Access

$550

per night

View Details

Key Amenities

  • Pool
  • Private Pool

About this property

Welcome to Ocean's Edge! A massive gulf front penthouse located right on Siesta Beach in a newly constructed building. With amazing views, a heated pool, and enough room to sleep up to 8, it is the only way to experience Siesta Key!Ocean's Edge is a luxuriously appointed penthouse in an extremely ...

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Property Type

Siesta Key Condo

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Sarasota-Siesta Key Coastal Five Bedroom with Pool and Spa

5 BR | 4 BA | Sleeps 13 | Quick View

Distance to beach: 400 feet to Siesta Beach

$395

per 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, Pool, Hot Tub And BBQ Area Within A Screen Enclosure. There Is A Nice Sized Sunning Patio As Well With Views Down The Waterway. This Home Entertains Excellent Because The Pool Area Is On ...

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Property Type

Siesta Key House

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"Fiji" 378 Canal Rd.

1 BR | 1 BA | Sleeps 4 | Quick View

$97

per night

View Details

Key Amenities

  • Air Conditioning
  • Kid Friendly
  • Pool
  • Private Pool

About this property

1 Bedroom King Bed, queen sleeper, screened porch. Pool Access, WIFI *W&D access, and ground floor.

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Property Type

Siesta Key Condo

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Sweet Siesta Key Resort Condo

1 BR | 1 BA | Sleeps 4 | Quick View

Distance to beach: 0.5 miles to Siesta Key Main Beach

$95

per night

View Details

Key Amenities

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

About this property

Sweet and Renovated (all new!) spacious one bedroom condo (can sleep 4) in a Siesta Key Luxury Resort Building - Harbor Towers Yacht & Racquet Club. Great views from all rooms of the historic waterfall in front of building, Palm Trees and Blue Skies. 2 Pools (1 for kids), Fitness Room, 3 lighted ...

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Property Type

Siesta Key Condo

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Updated 3 Bed/2 Bath House 5min walk to Siesta Key Beach, Heated Pool

$83

per night

View Details

Key Amenities

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

About this property

Beautiful 3 bedroom 2 bathroom house situated in the quiet, secluded neighborhood of Palm Island within minutes of all that Siesta Key has to offer. This well appointed house is a short 5 minute walk to the famous beaches of Siesta Key Beach (private beach access 10) and a 15 minute walk to the exciting ...

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Property Type

Siesta Key House

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Villa De Paradisio

4 BR | 2 BA | Sleeps 12 | Quick View

$385

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Welcome to the beautiful Villa De Paradisio! This gorgeous waterfront cottage is a very luxurious and large four [4] bedroom canal front heated pool home with two bathrooms in approximately 1,800SF of air conditioned living space with a heated pool overlooking the dock and canal. This home has been completely ...

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Property Type

Siesta Key House

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Coconut Grove – 6BR/6BA Private Heated Pool in the heart of Siesta Village

$404

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Welcome to Coconut Grove! A private home nestled right in the heart of the Siesta Village with the style, elegance and charm of Siesta Key. Enjoy a family home that sleeps 16, a private heated pool, and quite literally in the heart of Siesta Village!Coconut Grove features a unique combination of two ...

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Property Type

Siesta Key House

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SIESTA KEY HEAVEN

2 BR | 2 BA | Sleeps 4 | Quick View

$171

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

WE WE HAVE THE ABSOLUTE BEST SPOT ON THE ABSOLUTE BEST BEACH! (Reuters, May 27, 2011) 7 day Sat to Sat minimum stay.You will not find a more-convenient location or a better view anywhere else on the key! To take a couple short tours, see more photos, and to make your reservation without any service fees ...

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Property Type

Siesta Key Condo

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The Seascape – 8BR/9BA Beachfront, Heated Shared Pool, Private Access to Beach

$1100

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool
  • Private Pool

About this property

Welcome to The Seascape! The Seascape is the combination of two massive gulf front penthouses located right on Siesta Beach in a newly constructed building. With amazing views, a heated pool, and enough room to sleep up to 16, it is the only way to experience Siesta Key.The Seascape is the unique ...

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Property Type

Siesta Key Condo

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Casita Bayou

2 BR | 1 BA | Sleeps 6 | Quick View

$143

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool

About this property

Welcome to Casita Bayou!Casita Bayou is the larger half of this uniquely configured private home called the Coconut Bayou Cottage and it is the perfect escape for you and your guests. This side of the gorgeous home has recently been updated with new furnishings and completely renovated on the interior. ...

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Property Type

Siesta Key House

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Siesta Key Beachfront 3 Bedroom Private Home W/Full Gulf Views!

3 BR | 3 BA | Sleeps 7 | Quick View

3

Distance to beach: 300 feet to Siesta Beach

$395

per 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

"Wonderful Location!"
Reviewed March 25, 2019

We had a great stay! We visited for spring break with our two school-age kids and their grandparents. The location was fantastic - right on the beach with your own private path to the beach, and near ...

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Seaside Cottage

4 BR | 3 BA | Sleeps 10 | Quick View

1

$294

per night

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Key Amenities

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

About this property

Welcome to Seaside Cottage! A 4 bedroom, 3 bathroom vacation home with a heated pool is across the street from the No. 1 beach in the world! Hop on the trolley or a bike for easy access to Siesta Village. Enjoy the best of island living! Welcome to Seaside Cottage! This lovely and rare 4 bedroom 3 bathroom ...

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Property Type

Siesta Key Cottage

"Wonderful"
Reviewed May 3, 2018

Great place, very comfortable beds, all the items you need - kitchen equipped with great tools. Very clean.

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"Village Resort" 318 Canal Rd.

2 BR | 2 BA | Sleeps 6 | Quick View

Owner special: Off season special! 20% discount May 18- 25.

$151

per night

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Key Amenities

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

About this property

(upstairs) - 2 bed/ 2 bath- 1 king, 1 queen, queen sleeper, private laundry room, full kitchen including DW, heated pool, great back yard for BBQ and gathering.

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Property Type

Siesta Key Condo

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"Village Resort" 320 Canal Rd.

$151

per night

View Details

Key Amenities

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

About this property

(downstairs) - 2 bed/ 2 bath- 1 king, 1 queen, queen sleeper, private laundry room, full kitchen including DW, heated pool, great back yard for BBQ and gathering.

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Property Type

Siesta Key Condo

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La Contento Casa

3 BR | 2 BA | Sleeps 8 | Quick View

$385

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Welcome to the completely remodeled, and newly furnished La Contento Casa! This lovely 3 bedroom, 2 bath home comfortably sleeps 6 in beds, with ultra deluxe rollaway beds for an extra 2. Enjoy the peacefulness of a large heated pool with beautiful and breathtaking views of the water via the Intracoastal ...

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Property Type

Siesta Key House

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Juicy Mango Cabana

2 BR | 2 BA | Sleeps 6 | Quick View

$143

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly
  • Pool

About this property

Welcome to the Juicy Mango Cabana! This beautiful and vibrant 2 bedroom, 2 bathroom vacation home accommodates up to 6 people. Part of Mango Manor, Juicy Mango Cabana can be reserved alone or along with Honey Mango Cabana for big families or groups. Welcome to the Juicy Mango Cabana! This beautiful and ...

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Property Type

Siesta Key House

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Beautifully renovated condo, walk to Siesta Key Beach! See Special Summer Rate!

2 BR | 2 BA | Sleeps 4 | Quick View

1

Distance to beach: 0.5 miles to Siesta Key Beach

$100

per 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

"Great location, clean and updated 2BR/2BA condo!"
Reviewed February 4, 2019

We enjoyed our stay, wish it was available again next year. Great location, close to the beach, a nice walk to the village, beautiful view of the inter coastal. On the trolley stop to go north or south. ...

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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!