Siesta Key Vacation Rentals

(206 rentals)
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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LAST MINUTE March 1-31, 2019 * Fantastic Bay View * Siesta Key * Pool * Tennis *

2 BR | 1.5 BA | Sleeps 4 | Quick View

LAST MINUTE DEAL 3/1 - 3/23: WOW ! Hurry up - March calendar is filling up quickly Book at the #1 Beach in the USA

$125

per night

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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
Sea Grape Cottage

5 BR | 3.5 BA | Sleeps 12 | Quick View

2

$286

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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Sea la Vie – 5321 (R)

3 BR | 2 BA | Sleeps 8 | Quick View

$206

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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Seaside Cottage

4 BR | 3 BA | Sleeps 10 | Quick View

1

$286

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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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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Casita Playa

2 BR | 1 BA | Sleeps 4 | Quick View

$146

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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Serenity Cottage

3 BR | 3.5 BA | Sleeps 8 | Quick View

$206

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Welcome to Serenity Cottage!A pristine and elegant home so close to the most beautiful beach in the world most would say, Serenity Cottage offers a delightful and relaxing retreat with maximum comforts in mind, and a spacious abode designed around the needs and comforts of large families traveling ...

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Property Type

Siesta Key House

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Juicy Mango Cabana

2 BR | 2 BA | Sleeps 6 | Quick View

$146

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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Pura Vida Oasis

5 BR | 3 BA | Sleeps 13 | Quick View

$621

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Welcome to Pura Vida Oasis, a canal front cottage with heated pool & spa features 5 bedrooms/3 baths and can sleep up to 13. Enjoy eclectic wine storage rack, private dock and amazing views. Close to beaches, Siesta Village & trolley stop. This spectacular bright cheerful, canal front cottage ...

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Property Type

Siesta Key House

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STEPS TO THE WHITE POWDERED SAND OF SIESTA KEY BEACH! COMPLETE RENOVATION 2017!

$127

per night

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Key Amenities

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

About this property

This Completely renovated in 2017 Two Bedroom, One Bath condo with a view of the beach is just steps to the white, powdered-sugar sand of Siesta Key . Here at La Siesta Condominiums you also have easy access to Siesta Village and it's numerous restaurants, specialty shops, night life and other attractions.Unit ...

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Property Type

Siesta Key Condo

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Casa Ohana

4 BR | 3 BA | Sleeps 12 | Quick View

1

$326

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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"Tropical Tree House" 6151 Midnight Pass Rd.

1 BR | 1 BA | Sleeps 4 | Quick View

Owner special: LAST MINUTE SPECIAL 20% OFF MARCH 9- 23! $742 PER WEEK PLUS TAX AND CLEANING

$81

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

1 Bedroom - 1 Bath, upstairs (over carport) full kitchen. King bed, Queen sleeper sofa, living room opens to screened porch. WIFI, heated Pool .

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Property Type

Siesta Key House

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THE BLUE HOUSE - LUXURY VILLA SIESTA KEY- 10 PERS. 2 MN FROM THE BEACH

$695

per night

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Key Amenities

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

About this property

This beautiful high-tech house UNIQUE on 3 levels, has the added advantage of being at 2 minutes walk from one of the beaches ranked among the five most beautiful in the world. Located in the popular Island Circle (heart-shaped), from one of the two living rooms and kitchens you can enjoy directly the ...

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Property Type

Siesta Key House

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Newly updated 3 Bedroom 2 Bathroom House 5min walk to Siesta Key Beach

$83

per night

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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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MAGNOLIA 317-319

4 BR | 4 BA | Sleeps 12 | Quick View

Distance to beach: 0.3 miles to SIESTA KEY BEACH

$167

per night

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Key Amenities

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

About this property

PRICE PER INDIVIDUAL UNIT. DUPLEX: 1 UPSTAIRS UNIT AND 1 DOWNSTAIRS UNIT. SHORT WALK TO VILLAGE, OR BEACH. PRIVATE HEATED POOL, TIKI HUT, GRILL, EACH UNIT HAS OWN WASHER AND DRYER IN UNIT, FULL KITCHENS, WALK TO GROCERY STORE, GIFT SHOPS, RESTURANT'S, ICE CREAM STORE AND BARS.

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Property Type

Siesta Key Apartment

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103 - El Presidente Condo on Siesta Key

$191

per night

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Key Amenities

  • Full Kitchen

About this property

Spend your vacation in this beautiful coastal living inspired condo, just steps to the pool and beach in a gated community located on the white sands of Siesta Key’s Crescent Beach. The recently renovated, well lit and fully equipped kitchen boasts granite countertops, new appliances and a breakfast ...

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Property Type

Siesta Key Condo

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Sophie’s Quartier

6 BR | 5 BA | Sleeps 16 | Quick View

$586

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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JANUARY Cancel $5,400! Prestigious BEACHFRONT Complex. Updated Condo 1640 sq ft.

2 BR | 2 BA | Sleeps 4 | Quick View

Distance to beach: 1 feet to ON-SITE

$123

per night

View Details

Key Amenities

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

About this property

1,640 sq ft condo. Sleeps 4.MINIMUM ONE MONTH RENTAL POLICY AT CASARINA.NO SMOKING PERMITTED. NO PETS ALLOWED.For reviews, see VRBO #411994Casarina is one of the most prestigious beachfront buildings on Siesta Key (Sarasota, Florida), with the #1 rated beach in the United States (by Dr ...

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Property Type

Siesta Key Condo

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208 - El Presidente Condo on Siesta Key

$374

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

Newly renovated 2500+ sq. ft. 3 BR/3BA! King in master and large guest room and 2 twins in smaller guest room. 2 walk-in showers and 1 tub/shower combo. Price includes occupancy for 6. Flat screens in all bedrooms. Washer/dryer in unit. Parking Space #20

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Property Type

Siesta Key House

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405 - El Presidente Condo on Siesta Key

$208

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

Nice 2BR/2BA Gulf View unit that sleeps 4. Grab bars in master bath. Washer & dryer in unit! Parking Space #44

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Property Type

Siesta Key House

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310 - El Presidente Condo on Siesta Key

$482

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

Parking Space #17 Beautiful Gulf Front unit. 3BR 3Bath all remodeled. Gorgeous Gulf View

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Property Type

Siesta Key House

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The Grand Canal Cottage - One of The Cottages on the Key

$495

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Welcome to The Grand Canal Cottage, one of Siesta Key's most enchanting canal-front cottages, with private heated pool & spa. This idyllic 5 bedroom/4 bathroom home is just a short walk to Siesta Key Village and 2 blocks from Siesta Key Beach, voted the # 1 beach in the USA! The Grand Canal Cottage ...

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Property Type

Siesta Key House

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Villa Champagne

4 BR | 3 BA | Sleeps 8 | Quick View

1

$286

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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402 - El Presidente Condo on Siesta Key

$208

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

Newly renovated 2 bedroom/2 bath unit with bright and open floor plan. All new stainless steel appliances in updated kitchen. Beautiful gulf view from living room and master bedroom. Wood style tile floors thoughout with lovely Floridian lifestyle feeling. Washer/Dryer in utility room. No landline telephone. ...

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Property Type

Siesta Key House

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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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Siesta Key Beachfront Condo with Gulf View!

$135

per night

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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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Siesta Key 4 Bd, 3 Bathroom Waterfront Home w/Pool/Spa/steps to Siesta Beach

4 BR | 3 BA | Sleeps 8 | Quick View

Distance to beach: 400 yards to Siesta Beach

$395

per night

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Key Amenities

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

About this property

Oh What A Great Feeling You Get When You Are Looking Out at The Relaxing Waters Of The Grand Canal. This Home Is Special With 189 Ft. Of Canal Wrapping The Back Of The Home So You Get To Enjoy The Views From Many Rooms. Open All The Patio Doors To Feel The Tropical Breeze And Get Into That Relaxed Florida ...

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Property Type

Siesta Key House

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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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106 - El Presidente Condo on Siesta Key

$208

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool

About this property

Great 2BR/2BA with wonderful Gulf Views from living room, master bedroom and large balcony! Completely remodeled in Fall of 2016 with everything new! Stainless appliances, bright decor, ceiling fans and flat screen TV's in all rooms! King in master, 2 Queens in guest room and sofa sleeper in living room. ...

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Property Type

Siesta Key Condo

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What a view of the waterway!

2 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 500 feet to Crescent Beach

$143

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool

About this property

Welcome to Midnight Cove II and thanks for checking us out! We think we are quite spectacular if we must say so ourselves! Siesta Key and our local community are brimming with shopping, dining, art and culture. Ride the Siesta Key Breeze Trolley – it’s FREE and find relief knowing you won’t ...

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Property Type

Siesta Key Condo

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Villa De Paradisio

4 BR | 2 BA | Sleeps 12 | Quick View

$214

per night

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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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308 - El Presidente Condo on Siesta Key

$374

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

Enjoy the beautiful view from this newly remodeled and updated 3 Bedroom 3 Bath Executive Unit.2 Walk-in Showers, Flat screen TV's in all bedrooms. Washer/Dryer Parking Space #23

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Property Type

Siesta Key House

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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 Nautilus

8 BR | 6 BA | Sleeps 24 | Quick View

1

$102

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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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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Luxury Beach Cottage on Gulf

1 BR | 1 BA | Sleeps 2 | Quick View

$229

per night

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Key Amenities

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

About this property

New Luxury Cottage with tongue and groove wood cathedral ceilings, white wood floors, marble and tile bath, new appliances including washer, dryer, dishwasher, microwave located on two beautifully landscaped acres on the Beach. Big glass sliding doors to enjoy view of gardens. Koi ponds with waterfalls, ...

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Property Type

Siesta Key Cottage

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

3 BR | 3 BA | Sleeps 7 | Quick View

2

Distance to beach: 300 feet to Siesta Beach

$395

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen

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

"Stunning views!"
Reviewed January 9, 2019

This house is absolutely gorgeous! We enjoyed everything about it- The house itself including the inside amenities as well as the spectacular views from every room, the location right on the beach, & the ...

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504 - El Presidente Condo on Siesta Key

$208

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool

About this property

Welcome to our Siesta Key home located directly on the world famous white sand Crescent Beach! This unit was privately owned for almost 20 years and has been recently made available for rental. Our condo was totally remodeled in the last 12 months, meticulously maintained, 2 bedroom, 2 bath, with a breathtaking ...

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Property Type

Siesta Key House

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209 - El Presidente Condo on Siesta Key

$224

per night

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Key Amenities

  • Full Kitchen

About this property

Great 2BR/2BA with wonderful Gulf and beach Views from living room, master bedroom and large balcony! Less than 50 feet away and your feet will enjoy the sugary white power sands of the #1 beach in the US.

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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
Owner special: Special 20% off for summer June 1 -Aug 31. Two week minimum stay required. Don't miss this offer!!

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 double 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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Condo on Private Beach Monthly Only

Inquire for rates

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Key Amenities

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

About this property

We are located within a few blocks of siesta village. We are on our own private beautiful beach on the Gulf. Our property includes 2 heated pools, gym, lounges, library, pool. And secured parking. My condo has 3 queen beds, livingroom facing the Gulf, 2 bedrooms, 2 baths, full kitchen and dining room. ...

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Property Type

Siesta Key Condo

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Casa De Mariposa

6 BR | 6 BA | Sleeps 16 | Quick View

$396

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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Crescent Cottage

4 BR | 3 BA | Sleeps 10 | Quick View

$286

per night

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Key Amenities

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

About this property

Welcome to our beautiful and serene vacation home! A gorgeous beach cottage in a dream destination, Crescent Cottage offers a fun-filled activity-packed vacation plan with all of its great amenities, awesome location so close to the beach, and a spacious abode designed around the needs and comforts of ...

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Property Type

Siesta Key House

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204 - El Presidente Condo on Siesta Key

$191

per night

View Details

Key Amenities

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

About this property

Parking Space #10 Newly renovated beautiful open concept kitchen and living room. Granite counter tops throughout and beautiful glass walk-in shower in master bath with grab bar. Queen size sleeper sofa, 3 tvs, tile floors and washer/dryer. Beach towels and umbrella included.

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Property Type

Siesta Key Condo

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202 - El Presidente Condo on Siesta Key

$191

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

Updated 2 Bedroom 2 Bath decorated with a relaxed beach theme with all the amenities... 3 flat screens TV's, HD cable, DVD, stereo, secured wireless internet, washer and dryer in separate utility room, king size bed in master with attached bath with walk in shower with grab bar, hair dryer, two full size ...

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Property Type

Siesta Key House

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

$206

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Welcome to Pinacolada! 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!Pinacolada is one-half of the exquisite "Coconut ...

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Property Type

Siesta Key Townhome

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EP-207 - El Presidente Condo on Siesta Key

$224

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

Beautiful remodeled and decorated gulf view 2BR/2BA condo. Balcony to enjoy the view and gulf breeze and nice accommodations to entertain and enjoy Siesta Key Beach living. Only steps to the pool, the powdery white sand beach and pristine Siesta Key Waters. 

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Property Type

Siesta Key House

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301 - El Presidente Condo on Siesta Key

$233

per night

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Key Amenities

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

About this property

1840 SQUARE FOOT, largest 2 bedroom/2 bath unit in the building, with a wrap around balcony accessible from the Sun Room, a second balcony off the living room and master bedroom. Our apartment has been completely renovated and updated for your enjoyment. The master bedroom has a king size bed, ceiling ...

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Property Type

Siesta Key Apartment

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

$396

per night

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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 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!