Siesta Key Rentals Make It Easy to Plan a Tropical Getaway

Planning a trip to the home of the finest white sand beaches is quite exciting, especially with the prospect of several Siesta Key rentals found on the shoreline for easy access to this town’s famous 8-mile beach. Siesta Key, Florida is a popular getaway for families, honeymooners and retirees alike all year-long.

Find Your Favorite Amenities in Siesta Key Rentals


Siesta Key vacation rentals offer everything from Jacuzzis to direct access to the water, including entertainment areas and top-notch sound and theater systems for a comfy night in. Apartments and Siesta Key condo rentals are great options for extremely large groups that require several units very near each other too.

Siesta Key Vacation Rentals Place You in the Middle of Nature’s Wonders


If you choose one of the Siesta Key rentals located on the beach, you’ll be able to walk directly out to the ocean every morning and possibly spot one of the area’s resident dolphins or manatees frolicking in the water. You can also decide to take a walk along the streets to view the many varieties of tropical flora and fauna around many Siesta Key vacation rentals.

Siesta Key condo rentals may also offer equipment to take part in one of the many popular water sports in the area, such as snorkeling, jet skiing and even parasailing. There are also additional activities that any group staying in Siesta Key rentals will love taking part in to fully appreciate their surroundings.

Resort Life near Siesta Key Condo Rentals


This town is an especially popular resort area with plenty of relaxing and luxurious options available to visitors too. Many Siesta Key vacation rentals are within a short walking distance to one of the area’s many spas or salons if you prefer a day of massages and pedicures during your trip. No matter what you reasons for visiting this welcoming tropical getaway, Siesta Key condo rentals are the ideal choices whether you plan on a simple and relaxing vacation or an adventure-filled stay; either way, you’ll have a comfortable place to call "home" at the end of the day! Begin your search today! '

Expand your search for Florida vacation rentals to include Miami vacation rentals and Ft. Lauderdale rentals in South Florida, Destin vacation rentals and Marco Island rentals on the Gulf Coast, or Orlando vacation rentals near Disney.


Siesta Key Rentals

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Spectacular Ocean Front Crystal Sands Condo May 31- July 3 open 2week min.

— Property 182546
Siesta Key condo rental - Photo taken from the balcony at sunset
2 Bedrooms, Sleeps 6,
Condo, 2 Bathrooms, beach, waterfront, air-conditioning
Rates - per property (USD)
$1,295 - $1,885/week
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4-Story Luxury Villa Gulf and Village Views

— Property 274808
Siesta Key house rental - 4-Story Luxury Villa with Gulf and Village Views
3 Bedrooms, Sleeps 8,
House, 4 Bathrooms, 1 Half Bath, beach, near the ocean, pool
Rates - per property (USD)
$1,750 - $2,700/week
$4,500 - $7,500/month
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Siesta Key Florida - 2 Bedroom/2 Bath with Heated Pool, Tennis, Private Beach

— Property 193244
Siesta Key townhome rental - A view of our family room
3 Bedrooms, Sleeps 6,
Townhome, 2 Bathrooms, beach, waterfront, satellite or cable
Rates - per property (USD)
$648 - $1,000/week
Calendar Updated Feb 9 2010

Property Review

This condo is an end unit on the top floor. Extremely quiet with huge master bedroom and large 2nd bedroom. The condo has new kitchen, raised ceilings, and a glassed in lanai where you can watch...
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Gulf view & steps from beach and village - luxury Townhouse - 15% off in Jan!

— Property 231204
Siesta Key condo rental - Contemporary, new condo steps from the beach
3 Bedrooms, Sleeps 8,
Condo, 3 Bathrooms, 1 Half Bath, beach, village, jacuzzi
Rates - per property (USD)
$1,490 - $2,190/week
$4,700 - $6,800/month
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House of Sun - Gulf View Condo - 3rd Level - 2 BR/2 BA - Siesta Key Beach

— Property 193245
Siesta Key condo rental - A view of our beautifully furnished living room
2 Bedrooms, Sleeps 6,
Condo, 2 Bathrooms, beach, waterfront, pool
Rates - per property (USD)
$150 - $400/night
$895 - $1,795/week
Calendar Updated Feb 9 2010

Property Review

We hope to come back in the future. We had a lovely time!
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Gulfside Siesta Key Condo - Fun in the Sun!

— Property 214021
Siesta Key condo rental - Enjoy our beautiful white sand beach
2 Bedrooms, Sleeps 6,
Condo, 2 Bathrooms, beach, resort, pool
Rates - per property (USD)
$150 - $300/night
$695 - $1,495/week
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Resort across from Crescent Beach! All NEW!

— Property 126696
Siesta Key townhome rental - Lanai off master bedroom and living room
2 Bedrooms, Sleeps 6,
Townhome, 2 Bathrooms, beach, resort, sauna
Rates - per property (USD)
$895 - $1,231/week
Calendar Updated Feb 9 2010

Property Review

The accomodations were lovely, and made us feel right at home. The rooms were large with beautiful views. The furnishings and decor were comfortable, beautiful, clean, and everything was in...
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Gulf & Bay Bayside 3 BR w/ Bay Views

— Property 151436
Siesta Key townhome rental - Master Bdrm screened Balcony
3 Bedrooms, Sleeps 6,
Townhome, 2 Bathrooms, beach, resort, tennis court
Rates - per property (USD)
$1,142 - $1,495/week
Calendar Updated Feb 9 2010

Property Review

Description and photos reflect accurately this rental town home. We enjoyed the pool right across the from the home and the reasonable walk to the beautiful beach. We all agreed that this is a...
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White Sands Village 903 - Ideal place to enjoy your stay on Siesta Key

— Property 275309
Siesta Key condo rental - Crescent Beach
1 Bedroom, Sleeps 4,
Condo, 1 Bathroom, beach, resort, sauna
Rates - per property (USD)
$363 - $788/week
$1,300 - $3,000/month
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Siesta Key Ultimate Five-Star Luxury!

— Property 275353
Siesta Key condo rental - Beachfront Living Room
3 Bedrooms, Sleeps 6,
Condo, 2 Bathrooms, beach, waterfront, pool
Rates - per property (USD)
$2,100 - $2,550/week
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Beachfront Condo Beautiful Crystal Sands Siesta Key Sarasota Fl

— Property 158696
Siesta Key condo rental
2 Bedrooms, Sleeps 7,
Condo, beach, waterfront, balcony
Calendar Updated Feb 9 2010

Property Review

We loved the area, and the unit. This is a great location to kick back and enjoy a very quiet restful vacation. It is also convenient to activities, if you wish to have an active vacation as...
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Crystal Sands Villa #7-Beachside Villa on Beautiful Crescent Beach- Fall Special

— Property 212972
Siesta Key villa rental - Villa #7 at Crystal Sands
2 Bedrooms, Sleeps 6,
Villa, 2 Bathrooms, beach, pool
Rates - per property (USD)
$900 - $1,250/week
Calendar Updated Feb 8 2010

Property Review

This villa is among one of the best I've rented, and at a great price during high season. The villa is spacious and inviting, with every detail attended to by the owner. Just pack a bag,...
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Great Spacious 3 Bedroom Unit, Bayside at the Beautiful Gulf

— Property 155419
Siesta Key condo rental - Siesta Key
3 Bedrooms, Sleeps 8,
Condo, 2 Bathrooms, near the ocean, pool
Rates - per property (USD)
$1,395/week
Calendar Updated Feb 8 2010

Property Review

It is a great and calm and safe place. 2 Pools and 2 Tenniscourts. Really friendly for a holiday stay with the whole family. I is clean and fully equipped. Close to the public beach. It has a good...
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Poolside Villa - Polynesian Gardens

— Property 142744
Siesta Key villa rental - Fishing Dock
2 Bedrooms, Sleeps 4,
Villa, 1 Bathroom, 1 Half Bath, beach, near the ocean, pool
Rates - per property (USD)
$900 - $950/week
$3,600 - $3,800/month
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El Presidente Renovated Beachfront Condo on White Sand Beach-DISCOUNTS

— Property 183651
Siesta Key condo rental - View of El Presidente from the beach
2 Bedrooms, Sleeps 6,
Condo, 2 Bathrooms, beach, waterfront, jacuzzi
Rates - per property (USD)
$1,193 - $1,631/week
Calendar Updated Feb 8 2010

Property Review

Our family spent a week at this beautifully renovated condo. Great location right on Crescent Beach. Walk downstairs to the heated pool, step through the gates to the beautiful powdered sugar...
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Beach - Private Beach Access at the Shells Villa (Townhome)

— Property 228042
Siesta Key villa rental - Exterior view from gated yard.
3 Bedrooms, Sleeps 8,
Villa, 2 Bathrooms, 1 Half Bath, beach, village, garden
Rates - per property (USD)
$1,200 - $1,750/week
$3,000 - $5,600/month
Calendar Updated Feb 8 2010

Property Review

My family and I have rented homes in the past, but this one was the best experience we've had. The home is decorated beautifully and the location is amazing. Right on the beach and the village...
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NEWEST Beachfront Property - Luxury Penthouse!

— Property 170390
Siesta Key condo rental - Beach Pool
2 Bedrooms, Sleeps 4,
Condo, 2 Bathrooms, beach, balcony
Rates - per property (USD)
$1,595/week
$7,000 - $7,900/month
Calendar Updated Feb 8 2010

Property Review

I have stayed in Siesta Key for almost 20 years - first time at this property and the best experience ever! This is a first rate property. The condo itself is extremely well furnished. High...
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Siesta Sunsets at Fisherman's Cove

— Property 202264
Siesta Key condo rental - Fisherman's Cove Condo - Beachfront on Siesta Key
2 Bedrooms, Sleeps 6,
Condo, 2 Bathrooms, beach, waterfront, pool
Rates - per property (USD)
$1,045 - $1,645/week
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Beachfront Condo - Three Bedroom - Luxury

— Property 113929
Siesta Key condo rental - Fisherman's Cove Condo - Beachfront on Siesta Key
3 Bedrooms, Sleeps 8,
Condo, 2 Bathrooms, beach, waterfront, air-conditioning
Rates - per property (USD)
$1,545 - $2,095/week
Calendar Updated Feb 9 2010

Property Review

This was the perfect place to get away with great frinds for a week. I love to open all the windows to hear the ocean and feel the ocean breeze. Even on a rainy afternoon, you feel like you are...
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Deluxe Town home, Private Pool 1-4 Bedrooms

— Property 177153
Siesta Key townhome rental - Seaside Villas Luxury Townhome; 1-4 Bedrooms
4 Bedrooms, Sleeps 12,
Townhome, 3 Bathrooms, 1 Half Bath, beach, village, pool
Rates - per property (USD)
$1,495 - $2,045/week
Calendar Updated Feb 9 2010

Property Review

This place had it all. Great location in Siesta Key village and within easy walking distance to everything including beach, shopping, groceries, bars, restaurants and pretty much anything you...
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Deluxe Town home, Private Pool, 1-4 Bedrooms

— Property 118989
Siesta Key condo rental - Seaside Villas Luxury Townhome; 1-4 Bedrooms
1 Bedroom, Sleeps 4,
Condo, 1 Bathroom, near the ocean, resort, pool
Rates - per property (USD)
$625 - $900/week
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Siesta Key - Sundance Rental - Affordable - Key West Style - Private Pool

— Property 177152
Siesta Key apartment rental - Kitchen/dining area of two bedroom unit
2 Bedrooms, Sleeps 6,
Apartment, 2 Bathrooms, beach, village, terrace
Rates - per property (USD)
$885 - $1,210/week
Calendar Updated Feb 9 2010

Property Review

It has taken us awhile to get to you but we want to say thank you for a great stay at Siesta Key. The accommodations were exactly as you said, clean, contemporary, close and all that we wanted. ...
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Siesta Key - Sundance Rental - Affordable - Key West Style - Private Pool

— Property 118704
Siesta Key apartment rental - Sundance 1 to 6 Bedrooms
1 Bedroom, Sleeps 4,
Apartment, 1 Bathroom, beach, village, pool
Rates - per property (USD)
$600 - $825/week
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Island House Beach Resort

— Property 62186h
Siesta Key villa rental
2 Bedrooms, Sleeps 6,
Villa, 2 Bathrooms, coffee maker, toaster
Rates - per villa (USD)
$150 - $227/night
$1,050 - $1,589/week
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Island House Beach Resort

— Property 62179h
Siesta Key villa rental
2 Bedrooms, Sleeps 6,
Villa, 2 Bathrooms, coffee maker, toaster
Rates - per villa (USD)
$150 - $227/night
$1,050 - $1,589/week
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Island House Beach Resort

— Property 62192h
Siesta Key condo rental
2 Bedrooms, Sleeps 6,
Condo, 2 Bathrooms, coffee maker, toaster
Rates - per condo (USD)
$194 - $298/night
$1,358 - $2,086/week
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6148 Midnight Pass Rd

— Property 62204h
Siesta Key condo rental
2 Bedrooms, Sleeps 4,
Condo, 2 Bathrooms, coffee maker, toaster
Rates - per condo (USD)
$194 - $298/night
$1,358 - $2,086/week
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Island House Beach Resort

— Property 62207h
Siesta Key condo rental
2 Bedrooms, Sleeps 6,
Condo, 2 Bathrooms, coffee maker, toaster
Rates - per condo (USD)
$194 - $298/night
$1,358 - $2,086/week
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Island House Beach Resort

— Property 62215h
Siesta Key condo rental
2 Bedrooms, Sleeps 4,
Condo, 2 Bathrooms, coffee maker, toaster
Rates - per condo (USD)
$194 - $298/night
$1,358 - $2,086/week
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House of Sun 307 beach rentals condos Siesta Key Florida with Gulf Views

— Property 7011096h
Siesta Key condo rental - A view of our living room
2 Bedrooms, Sleeps 6,
Condo, 2 Bathrooms, coffee maker, cooking utensils
Rates - per condo (USD)
$150 - $300/night
$895 - $1,795/week
$2,898 - $5,406/month