Siesta Key Vacation Rentals

(202 rentals)
The Solaster

6 BR | 6 BA | Sleeps 20 | Quick View

$400

per night

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Key Amenities

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

About this property

The Solaster is a combination of two units (Casita Morning Star and Casita Sun Star) within walking distance of Point of Rocks Beach. Each unit has 3 bedrooms, 3 bathrooms, their own heated pool & a private screened in lanai. Ideal for large groups! Welcome to The Solaster! Our newly renovated luxury ...

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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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Casita Playa

2 BR | 1 BA | Sleeps 4 | Quick View

$143

per night

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Key Amenities

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

About this property

Welcome to Casita Playa of Playa y Blanca. This single level (2 BR/1BA - Master BR/1 Queen & 2nd BR/2 twins -sleeps 4) vacation home features private, gated beach access, a sparkling clean hot tub in a private, lush setting, a communal heated swimming pool with plenty of pool furniture and a bathroom, ...

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Property Type

Siesta Key House

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Siesta Towers #6F Gulf views and Downtown Sarasota Views. Siesta Key Village

2 BR | 2 BA | Sleeps 4 | Quick View

Distance to beach: 800 feet to Siesta Key Beach

$140

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • 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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*All New Villa* #1 Beach USA~ Gulfside Condo - Siesta Key

$149

per night

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Key Amenities

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

About this property

Our villa is a tastefully furnished and fully equipped with state of the art kitchen on the widest part of Crescent (Siesta Key) Beach. The villa is located GULFSIDE just steps to the beach, no streets to cross, It is just two villas away and a short 20 second walk.The villa sleeps 4-6 people, ...

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Property Type

Siesta Key Villa

"Stay in Barbara's Unit was wonderful again ! Best Beach EVER !!!!"
Reviewed February 4, 2019

Barbara's unit is so close to the beautiful Siesta Key beach....only steps away. Unit is outfitted with everything you can think of and then some !! Love the convenience of being able to park right ...

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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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Baybreeze – 3BR/3BA Private Heated Pool in the heart of Siesta Village

$214

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Welcome to Baybreeze! 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 8, a shared heated pool, and quite literally in the heart of Siesta Village!Baybreeze is one-half of the beautiful "Coconut Grove," ...

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Property Type

Siesta Key Townhome

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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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Seahorse Cabana

3 BR | 3 BA | Sleeps 8 | Quick View

$179

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

Welcome to the Seahorse Cabana!The Seahorse Cabana is one half of the uniquely configured private homes called the Sandy Seahorse Cottage and it is the perfect escape in the tropics of Siesta Key. This property can be rented separately or combined to accommodate a large party! This side of the gorgeous ...

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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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Siesta Key Gulf View Palm Bay Club in the Tower

$179

per night

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Key Amenities

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

About this property

Beautiful 2 Bedroom, 2 Full bath condo. Close to everything, right on Crescent Beach, voted #1 beach twice in the last 5 years. King in the master, 2 full size beds in the second.

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Property Type

Siesta Key Condo

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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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Midnight Cove II Bayside #734 Beautiful top floor condo overlooks bay

2 BR | 1.5 BA | Sleeps 5 | Quick View

Distance to beach: 250 feet to Siesta Key

$157

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • 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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Admirals Watch

3 BR | 3 BA | Sleeps 8 | Quick View

$354

per night

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Key Amenities

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

About this property

Welcome to Admirals Watch! This beautiful, luxurious and modern 3 bedroom, 3 bathroom, heated pool, townhome boasts the best views of the world famous No. 1 Siesta Key Beach Access! With absolutely unobstructed views, this home is part of only a handful of private residences that can claim such gorgeous ...

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Property Type

Siesta Key Condo

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Sand Dollar Cottage

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 Sand Dollar Cottage! This lovely 3 bedroom, 2 bath north Siesta Key vacaiton home comfortably sleeps 6 in beds, with a soft ultra plush sofa sleeper in the living room for an extra 2. Enjoy heated pool and waterview of Intracoastal canal. Welcome to the completely remodeled, and newly furnished ...

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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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Fern Haven Tropical Bungalow (Studio) - MONTHLY RENTAL

Studio | 1 BA | Sleeps 2 | Quick View

3

Distance to beach: 0.5 miles to Siesta Key Beach

$135

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly
  • Rentals by Owner

About this property

Fern Haven studio bungalow is a Key West style studio efficiency. It is comfy, cozy, bright and airy with French doors onto a deck overlooking gardens and brick patio and walkway to a shared hot tub. It has a large mirrored doored closet and under bed drawers for ample storage. It is situated in a quiet ...

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Property Type

Siesta Key Studio

"Fern Haven met our expectations and then some!"
Reviewed April 20, 2019

First of all, the bungalow itself- Exactly as picured on the webpages and clean and for such a small space, well equipped except for a two burner cook top and a portable oven stored in a cupboard under ...

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Beautiful 2 Bedroom Condo at Crescent Royale

$145

per night

View Details

Key Amenities

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

About this property

Beautiful 2 bedroom. 2 bath condo across the street from the Gulf of Mexico. Great view from the screened in lanai. Heated resort pool, gym, gas grills, parking and across the street from the public beach. Less that 1 mile from Siesta Key Village where you will find great restaurants and shopping. Siesta ...

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Property Type

Siesta Key Condo

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The Nautilus

8 BR | 6 BA | Sleeps 24 | Quick View

1

$514

per night

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Key Amenities

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

About this property

Siesta Key home perfect for groups up to 24! The Nautilus, a combo of the Casa Tegula and Casa Stolida homes, is walking distance to the beach. Each cottage has 4 bedrooms, 3 bathrooms, their own heated pool and private cabanas. Welcome to The Nautilus! Our newly constructed luxury home is now accepting ...

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Property Type

Siesta Key House

"Family Birthday Getaway"
Reviewed January 22, 2019

What a great vacation rental, just what we were looking for! Plenty of room for us all and close to restaurants, the beach and all the extras like bicycles, plenty of refrigerators etc. Definitely would ...

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Honey Mango Cabana

2 BR | 1 BA | Sleeps 6 | Quick View

$143

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

Welcome to the Honey Mango Cabana! This beautiful and vibrant 2 bedroom, 1 bathroom vacation home accommodates up to 6 people. Part of Mango Manor, Honey Mango Cabana can be reserved alone or along with Juicy Mango Cabana for big families or groups. Welcome to the Honey Mango Cabana! This beautiful and ...

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Property Type

Siesta Key House

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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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"Village Resort" 322 Canal Rd.

2 BR | 2 BA | Sleeps 6 | Quick View

1

$151

per night

View Details

Key Amenities

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

About this property

322 Canal Rd - Village Resort Just steps to #1 voted beach, restaurants, grocery’s, shops, bars & ice cream! (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 gatherings. Combine all four ...

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Property Type

Siesta Key Condo

"Awesome!"
Reviewed January 28, 2019

This property had the best location, close to beach and town!!!! I condo was very clean and had everything you need! The pool and back yard sanctuary was a nice bonus!! Hope to stay here again, would ...

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"SITTING ON THE DOCK OF THE BAY" "Coastal Courtyard" 6151 Midnight Pass Rd.

1 BR | 1 BA | Sleeps 4 | Quick View

Owner special: Off season special! 20% discount April 27- May 25.

$77

per night

View Details

Key Amenities

  • Air Conditioning

About this property

1 Bedroom - 1 Bath, upstairs, king bed, queen sleeper sofa, loveseat, kitchenette. Open deck, combines with Peaceful Waters to make 2 Bedroom/2 Baths. WIFI, Pool Access

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Property Type

Siesta Key House

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636onthekey - The “Belle” of the Beach

$357

per night

View Details

Key Amenities

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

About this property

The Belle of the Beach! Our beautiful Key West style home sits directly on Siesta Beach, voted the #1 beach in the USA, and is only 1/2 mile walking distance from the Village of Siesta Key!Our house is located directly on Siesta Beach! No need to move off of the balcony to see 180 degree sunset views ...

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Property Type

Siesta Key House

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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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La Casa Verde

4 BR | 2 BA | Sleeps 10 | Quick View

$440

per night

View Details

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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Sandy Cabana

3 BR | 3 BA | Sleeps 8 | Quick View

$179

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

Welcome to the Sandy Cabana!The Sandy Cabana is one half of the uniquely configured private homes called the Sandy Seahorse Cottage and it is the perfect escape in the tropics of Siesta Key. This property can be rented separately or combined to accommodate a large party! This side of the gorgeous ...

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Property Type

Siesta Key House

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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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Sea the View

4 BR | 3 BA | Sleeps 10 | Quick View

$440

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Welcome to Sea the View! This luxurious and exquisite home features 4 bedrooms and 3 full baths, a heated pool and spa, overlooking gorgeous water views of the grand canal, with easy access to Bay and Gulf by boat, and so very close to Siesta Key Beach! The views from the living and kitchen area as well ...

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Property Type

Siesta Key House

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Penthouse Condo Siesta Key, Amazing Views, Pools, Tennis, Gym, Beach

1 BR | 1 BA | Sleeps 2 | Quick View

Distance to beach: 0.1 miles to Siesta Key Main Beach

$150

per night

View Details

Key Amenities

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

About this property

Penthouse Condo on Siesta Key with WATER VIEWS , and Sunrise views too! available at Harbor Towers Yacht & Racquet Club - which offers Resort Living at the Beach! Harbor Towers has 2 heated pools, GYM/Suana/LockerRoom, 3 lighted tennis courts, Marina (can dock your boat for $5/nite), gym, locker ...

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Property Type

Siesta Key Condo

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Mango Manor

4 BR | 3 BA | Sleeps 12 | Quick View

$287

per night

View Details

Key Amenities

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

About this property

Welcome to the Mango Manor! A beautiful and vibrant 4 bedroom, 3 bathroom vacation home with a heated pool accommodates up to 12 people. The attractive property, a combination of Honey Mango Cabana & Juicy Mango Cabana, is perfect for large families. Welcome to the Mango Manor! This beautiful and ...

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Property Type

Siesta Key House

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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

$128

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

$164

per night

View Details

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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Casita Blanca

2 BR | 1 BA | Sleeps 4 | Quick View

$143

per night

View Details

Key Amenities

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

About this property

Welcome to Casita Playa of Playa y Blanca. This COMPLETELY RENOVATED, single level (2 BR/1BA - Master BR/1 Queen & 2nd BR/2 twins -sleeps 4) vacation home features private, gated beach access, a sparkling clean hot tub in a private, lush setting, a communal heated swimming pool with plenty of pool ...

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Property Type

Siesta Key House

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Closest Condo to the Gulf of Mexico on Siesta Key - Direct Oceanfront

2 BR | 2 BA | Sleeps 6 | Quick View

12

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

$171

per night

View Details

Key Amenities

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

"Best Vacation Condo in Siesta Key!"
Reviewed April 13, 2019

Dear Paul and Sheri,Fabulous Condo Fabulous View Fabulous Location Fabulous Info Book (We called it the Holy Grail) Fabulous Food Fabulous Vacation......! We definitely want to come back. The beds ...

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SIESTA KEY HEAVEN

2 BR | 2 BA | Sleeps 4 | Quick View

$171

per night

View Details

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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"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

View Details

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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Monarch Villa

3 BR | 3 BA | Sleeps 9 | Quick View

$214

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool
  • Private Pool

About this property

Welcome to Monarch Villa, a beautiful 3 bedroom, 3 bathroom townhome just steps from the beach. Along with its sister property Peacock Villa, reserve Casa de Mariposa for the ultimate corporate retreat, family reunion or destination wedding setting! Welcome to Monarch Villa! The luxurious three (3) bedroom, ...

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Property Type

Siesta Key House

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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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"Everglades" 378 Canal Rd.

2 BR | 2 BA | Sleeps 6 | Quick View

$143

per night

View Details

Key Amenities

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

About this property

2 Bd/2 Bath, King Bed, Two queen beds, Open Deck, ground floor. Pool Access, WIFI, *W&D access, and 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 ...

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Property Type

Siesta Key House

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Villa Vista Mare

3 BR | 3 BA | Sleeps 10 | Quick View

1

$334

per night

View Details

Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Oceanfront
  • Pool

About this property

Welcome to Villa Vista Mare! This beautiful and luxurious 3 bedroom, 3 bathroom, heated pool, townhome boasts the best views of the world famous No. 1 Siesta Key Beach Access! With absolutely unobstructed views, this home is part of only a handful of private residences that can claim such gorgeous and ...

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Property Type

Siesta Key Townhome

"Best ever..."
Reviewed May 27, 2018

This was the first time we have ever rent without see the property or at least know the owner. I was very nervous about the whole situation, as you can imagine. We were in Siesta Key for our daughters ...

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Siesta Dream House

4 BR | 3.5 BA | Sleeps 12 | Quick View

$254

per night

View Details

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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"Peaceful Waters" ON THE DOCK" 6151 Midnight Pass Rd.

$89

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

1 Bedroom - 1 Bath, upstairs, king bed, queen and twin sleeper sofas. Opens to a screen lanai with canal view, kitchen with serving bar, WIFI, Pool Access

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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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Sea Grape Cottage

5 BR | 3.5 BA | Sleeps 12 | Quick View

2

$271

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

Welcome to Sea Grape Cottage! The luxurious tri-level Siesta Key home features gourmet kitchen, heated pool with a sloped beach entry, hot tub, covered lanai with outdoor kitchen & 2-car garage. Perfect for a dream beach vacation for up to 12! Built in June 2017, this tri-level home completely captures ...

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Property Type

Siesta Key House

"Family vacation"
Reviewed July 14, 2018

Sea grape cottage is stunningly beautiful and fit our family of 13 with room to spare. The pool was a hit with everyone. The home is furnished with everything you need for a wonderful group vacation,

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"Village Resort" 320 Canal Rd.

$151

per night

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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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Villa Champagne

4 BR | 3 BA | Sleeps 8 | Quick View

1

$294

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Welcome to “Villa Champagne”, one of the most fabulous vacation homes in Siesta Key. It’s also one of the most popular favorites among our many guest families. The magic begins as you enter the foyer of this beautiful villa and gaze across the expansive living area, then further out ...

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Property Type

Siesta Key House

"Indian Rock Beach Vacation"
Reviewed July 2, 2018

GREAT Views / Great house on beach / Quiet Our family of 9 had a ball

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Casa De Mariposa

6 BR | 6 BA | Sleeps 16 | Quick View

$404

per night

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Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Pool
  • Private Pool

About this property

Welcome to Casa de Mariposa! This gorgeous property is comprised of two units, Monarch and Peacock Villa which are both mirror images of one another. Each unite features a 3 bedroom, 3 bathroom configuration with their very own common space to include a kitchen, dining area, private balconies, and private ...

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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!