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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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)
$1,042 - $1,395/week
Calendar Updated Nov 25 2009

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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Siesta Key 'A Barrier Island' Florida's Cultural Coast

— Property 188943
Siesta Key condo rental - Walk on the Beach
2 Bedrooms, Sleeps 6,
Condo, 2 Bathrooms, beach, waterfront, pool
Rates - per property (USD)
$1,665/week
Calendar Updated Nov 25 2009

Property Review

What a GREAT place to relax. This condo has all of the comforts of home. Dick & Connie always responded quickly to any questions we had,they made this rental a very pleasant experience. The views...
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Sophistication, Style & Serenity on Siesta Key: 'Casa de Mariposa': FALL SPECIAL

— Property 170576
Siesta Key townhome rental - Casa de Mariposa Beach Road View
3 Bedrooms, Sleeps 8,
Townhome, 3 Bathrooms, beach, village, pool
Rates - per property (USD)
$350 - $400/night
$2,600 - $2,900/week
$1,000 - $9,500/month
Accepts Online Payments
Calendar Updated Nov 25 2009

Property Review

My girlfriends and I all had the pleasure of staying in one of these gorgeous suites for a week. The house itself is huge, bright and excellently designed. It is also filled with charming family...
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Sophistication, Style & Serenity on Siesta Key: 'Casa de Mariposa':

— Property 170592
Siesta Key townhome rental - CDM View from Beach Access
3 Bedrooms, Sleeps 8,
Townhome, 3 Bathrooms, beach, village, terrace
Rates - per property (USD)
$300 - $375/night
$2,400 - $2,700/week
$8,500 - $9,500/month
Accepts Online Payments
Calendar Updated Nov 25 2009

Property Review

I truly do not think that I can find the words to accurately depict our feelings about the Casa, Bambi & her staff. Upon staying here the only thing that we were left wanting for was more...
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Charming Pool-Front Villa across from Crescent Beach

— Property 117588
Siesta Key villa rental - Poolside view of the lanai
3 Bedrooms, Sleeps 6,
Villa, 2 Bathrooms, beach, near the ocean, air-conditioning
Rates - per property (USD)
$900/week
$4,000/month
Calendar Updated Nov 25 2009

Property Review

Description was accurate and photos did show real premises. It was clean and well-maintained, lots of towels an linen provided, fully equipped kitchen, nice and daily maintained pool. Distance to...
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Charming Remodeled Beachfront Condo with Fabulous Views #212

— Property 150231
Siesta Key condo rental - Clean, modern & spacious condo
2 Bedrooms, Sleeps 6,
Condo, 2 Bathrooms, beach, near the ocean, air-conditioning
Rates - per property (USD)
$899 - $1,325/week
Calendar Updated Nov 25 2009

Property Review

This was our first experience at renting a condo online. It could not have gone any smoother. First of all the condo was even better than expected. It had all the amenities of home except for...
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Beautiful Gulf Front Condo-Ocean View **Rates Reduced**

— Property 248795
Siesta Key condo rental
2 Bedrooms, Sleeps 6,
Condo, 2 Bathrooms, beach, waterfront, sauna
Rates - per property (USD)
$846 - $1,526/week
Calendar Updated Nov 26 2009

Property Review

This condo is in a perfect location and in excellent condition. There are restaurants, shopping and a grocery store across the street. Everything is very convenient. We ate a lot at Captain Curts...
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Siesta Key FL Excelsior 309 Bay Views, Siesta Key Florida

— Property 7008907h
Siesta Key condo rental - A view of our beautifully furnished living room
2 Bedrooms, Sleeps 6,
Condo, 2 Bathrooms, air-conditioning, balcony
Rates - per condo (USD)
$1,930 - $3,980/month
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Beach & Surf at your Doorstep - Luxury Condo

— Property 118221
Siesta Key condo rental - View from the Lanai-Ocean is so close & beautiful!
2 Bedrooms, Sleeps 6,
Condo, 2 Bathrooms, 2 Half Baths, beach, waterfront, air-conditioning
Rates - per property (USD)
$920 - $1,645/week
Calendar Updated Nov 25 2009

Property Review

Our family stayed at at this beautiful condo for a week in May. The views are magnificent and the beach is not crowded. They condo is well stocked and absolutely beautiful! We had such a...
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Newly Remodeled Beachfront Condo with Full Ocean Views

— Property 152126
Siesta Key condo rental
2 Bedrooms, Sleeps 6,
Condo, 2 Bathrooms, waterfront, air-conditioning
Rates - per property (USD)
$899 - $1,325/week
Calendar Updated Nov 25 2009

Property Review

Our family of five stayed in this unit and it was great. The beach right across the street was beautiful and not overly crowded. We never had trouble finding a great spot. The unit had everything...
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Spacious, newly renovated Pool Home close to Siesta Key Beach

— Property 528834
Siesta Key house rental
3 Bedrooms, Sleeps 6,
House, 2 Bathrooms, 1 Half Bath, beach, near the ocean, garden
Rates - per property (USD)
$1,881 - $2,257/week
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Right on the Beach with Gulf Views and Heater Pool

— Property 259492
Siesta Key condo rental - View from Sun Deck
2 Bedrooms, Sleeps 6,
Condo, 2 Bathrooms, beach, resort, tennis court
Rates - per property (USD)
$130 - $258/night
$910 - $1,670/week
$4,000 - $6,000/month
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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 Nov 24 2009

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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Siesta Key Gulf and Bay Club Resort 207F Beach Front rentals, Siesta Key, FL

— Property 7008901h
Siesta Key condo rental - Relax and enjoy our wonderful gulfside condo
2 Bedrooms, Sleeps 6,
Condo, 2 Bathrooms, air-conditioning, beach
Rates - per condo (USD)
$2,898 - $5,802/month
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Tranquil Condo at Sandy Cove on Beautiful Siesta Key

— Property 252347
Siesta Key condo rental - Your Private Beach
1 Bedroom, Sleeps 2,
Condo, 1 Bathroom, lake, near the ocean, balcony
Rates - per property (USD)
$1,500 - $2,500/month
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Newly Remodeled Townhouse on Beautiful Siesta Key

— Property 246503
Siesta Key townhome rental - Heated swimming pool.
2 Bedrooms, Sleeps 6,
Townhome, 2 Bathrooms, 1 Half Bath, beach, village, pool
Rates - per property (USD)
$800 - $1,100/week
$2,400 - $3,500/month
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Private tropical retreat-a short walk from the beach

— Property 229034
Siesta Key villa rental - Dining room
2 Bedrooms, Sleeps 6,
Villa, 2 Bathrooms, near the ocean, air-conditioning
Rates - per property (USD)
$850 - $1,200/week
$2,500 - $3,400/month
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1st Floor/2 Bedroom Beach Walkout. Free Hi-Speed, 42'TV, May 2 Available

— Property 230433
Siesta Key condo rental - Our unit is above on the first floor
2 Bedrooms, Sleeps 6,
Condo, 2 Bathrooms, beach, pool
Rates - per property (USD)
$920 - $1,470/week
Calendar Updated Nov 23 2009

Property Review

We had them everynight of our stay and one night some dolphins made it even better by swimming across as the sun melted into the gulf. The condo was the perfect place for my husband and I but...
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Siesta Key Beach Villa

— Property 166106
Golf
Siesta Key villa rental - Island Style Villa - Lush Grounds 2 pools
1 Bedroom, Sleeps 4,
Villa, 1 Bathroom, 1 Half Bath, beach, waterfront, pool
Rates - per property (USD)
$107/night
$748 - $1,059/week
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Enchanting Beachfront 'Toes in the Sand' Condo

— Property 225835
Siesta Key condo rental - Put your toes in the sand, directly on the gulf!
2 Bedrooms, Sleeps 6,
Condo, 2 Bathrooms, beach, waterfront, pool
Rates - per property (USD)
$1,000 - $1,650/week
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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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Crescent Arms Villa

— Property 266312
Siesta Key cottage rental - Crescent Arms Villa
2 Bedrooms, Sleeps 5,
Cottage, 2 Bathrooms, beach, resort, pool
Rates - per property (USD)
$1,050 - $1,679/week
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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 Nov 24 2009

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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Siesta Key Vacation Rental at Siesta Sands Beach Resort

— Property 176748
Siesta Key condo rental - Private Tiki Hut on the beach
1 Bedroom, Sleeps 6,
Condo, 1 Bathroom, 1 Half Bath, beach, resort, balcony
Rates - per property (USD)
$600 - $1,175/week
Calendar Updated Nov 24 2009

Property Review

We had a wonderful stay at a beautiful property. Although the details above say that it had 1 1/2 baths, there was only 1. This was not a problem and I don't believe that we thought there was...
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Island House Beach Resort

— Property 62179h
Siesta Key villa rental
2 Bedrooms, Sleeps 6,
Villa, 2 Bathrooms, adventure, air-conditioning
Rates - per villa (USD)
$144 - $227/night
$1,008 - $1,589/week
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Island House Beach Resort

— Property 62197h
Siesta Key condo rental
2 Bedrooms, Sleeps 6,
Condo, 2 Bathrooms, adventure, air-conditioning
Rates - per condo (USD)
$186 - $298/night
$1,302 - $2,086/week
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Island House Beach Resort

— Property 62206h
Siesta Key condo rental
2 Bedrooms, Sleeps 6,
Condo, 2 Bathrooms, adventure, air-conditioning
Rates - per condo (USD)
$186 - $298/night
$1,302 - $2,086/week
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Island House Beach Resort

— Property 62194h
Siesta Key condo rental
2 Bedrooms, Sleeps 4,
Condo, 2 Bathrooms, adventure, air-conditioning
Rates - per condo (USD)
$186 - $298/night
$1,302 - $2,086/week
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Beach Road #201

— Property 71876h
Siesta Key villa rental
3 Bedrooms, Sleeps 6,
Villa, 2 Bathrooms, adventure, beach
Rates - per villa (USD)
$1,275 - $4,700/week
$3,800 - $5,800/month
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Island House Beach Resort

— Property 62212h
Siesta Key condo rental
2 Bedrooms, Sleeps 4,
Condo, 2 Bathrooms, adventure, air-conditioning
Rates - per condo (USD)
$186 - $298/night
$1,302 - $2,086/week