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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Beach Less than 5min walk to sand ,NEW KITCHEN Pool View New Furn,!Great Price!

— Property 251980
Siesta Key condo rental - Pool View from living room
2 Bedrooms, Sleeps 6,
Condo, 2 Bathrooms, beach, village, air-conditioning
Rates - per property (USD)
$700 - $1,200/week
$2,500 - $3,200/month
SPECIAL OFFER! 20% to 30% Discounts (August 29 - January 30)
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Beachwalk -- Luxury Townhouse

— Property 218634
Special Offer
Siesta Key townhome rental - Beachwalk - Luxury townhome with private elevator
3 Bedrooms, Sleeps 8,
Townhome, 2 Bathrooms, 1 Half Bath, beach, village, balcony
Rates - per property (USD)
$1,495 - $2,045/week
Calendar Updated Nov 13 2009

Property Review

This is our first vacation to Siesta Key & a memorable one at that! Not only was the weather great, but the pool was perfect as well! We felt like we were at home here! Nice touches - games,...
SPECIAL OFFER! 20% to 30% Discounts (August 29 - January 30)
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Siesta Sunsets at Fisherman's Cove

— Property 202264
Special Offer
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
SPECIAL OFFER! 20%-30% Discounts (August 30 - January 30)
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Beachfront Condo - Three Bedroom - Luxury

— Property 113929
Special Offer
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 Nov 13 2009

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...
SPECIAL OFFER! 20% - 30% Discounts (August 30 - January 2)
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Deluxe Town home, Private Pool 1-4 Bedrooms

— Property 177153
Special Offer
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 Nov 13 2009

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...
SPECIAL OFFER! 20% to 30% Discounts (August 29 - January 30)
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Deluxe Town home, Private Pool, 1-4 Bedrooms

— Property 118989
Special Offer
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
SPECIAL OFFER! 20%-30% Discounts (August 29 - January 30)
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Siesta Key - Sundance Rental - Affordable - Key West Style - Private Pool

— Property 177152
Special Offer
Siesta Key apartment rental - Sundance
2 Bedrooms, Sleeps 6,
Apartment, 2 Bathrooms, beach, village, terrace
Rates - per property (USD)
$885 - $1,210/week
Calendar Updated Nov 13 2009

Property Review

We rented this location just a few weeks prior to our trip deciding to try something different rather than just a hotel. We enjoyed it very much. They had thought of several of the little extras...
SPECIAL OFFER! 20% to 30% Discounts (August 29 - January 30)
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Siesta Key - Sundance Rental - Affordable - Key West Style - Private Pool

— Property 118704
Special Offer
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
SPECIAL OFFER! SAVE $400wk! Thanksgiving, Dec. & Jan.! (November 14 - January 31)
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Walk to Siesta Beach & Village /Spacious House/ Pool /On Canal

— Property 224280
Special Offer
Siesta Key house rental - Spacious living room
3 Bedrooms, Sleeps 6,
House, 2 Bathrooms, beach, waterfront, pool
Rates - per property (USD)
$1,500 - $2,300/week
$4,500 - $6,800/month
Calendar Updated Nov 13 2009

Property Review

This is the most beautiful home we have ever rented in the area. Its close to Siesta Beach and the Village. The screened lani was so perfect in the morning while having our coffee and looking out...
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Couples Bayside Paradise on Siesta Key Sarasota, FL (7 Night Minimum)

— Property 316221
Siesta Key townhome rental - Sunset Siesta Key Crescent Beach
1 Bedroom, Sleeps 3,
Townhome, 1 Bathroom, beach, near the ocean, sauna
Rates - per property (USD)
$798 - $1,100/week
Calendar Updated Nov 13 2009

Property Review

This was the most relaxing vacation ever. The rental was so comfortable and clean. It was well stocked with everything you would find at home. A trip to the market for food and you're set. The...
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All NEW! Beautiful and Luxurious! across from Crescent Beach!

— 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 Nov 13 2009

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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1st Floor Midnight Cove 1 Condo with Private Beach

— Property 318750
Siesta Key condo rental - Living Area With Relaxing Lani
2 Bedrooms, Sleeps 6,
Condo, 1 Bathroom, 1 Half Bath, beach, resort, tennis court
Rates - per property (USD)
$699 - $1,199/week
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Spectacular Location - Close to Everything!

— Property 172205
Siesta Key condo rental - Clubhouse and large heated pool
2 Bedrooms, Sleeps 6,
Condo, 2 Bathrooms, near the ocean, resort, sauna
Rates - per property (USD)
$697 - $1,197/week
$2,788 - $4,788/month
Calendar Updated Nov 13 2009

Property Review

The condo was very clean and cozy and quiet. I would give it a 5 star rating but there were some very minor problems. The light/exhaust fan in the master bedroom sounded like a boeing jet...
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Island House Beach Resort

— Property 62183h
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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Siesta Key Palm and Bay Club G88 tower renta, Siesta Key Florida

— Property 7029473h
Siesta Key condo rental - Enjoy Gulf views from our living room.
1 Bedroom, Sleeps 4,
Condo, 1 Bathroom, air-conditioning, balcony
Rates - per condo (USD)
$175 - $300/night
$895 - $2,100/week
$2,898 - $9,000/month
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Beach Road #202

— Property 71877h
Siesta Key villa rental
2 Bedrooms, Sleeps 6,
Villa, 3 Bathrooms, 1 Half Bath, adventure, beach
Rates - per villa (USD)
$1,600 - $2,500/week
$4,200 - $6,500/month
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Island House Beach Resort

— Property 62178h
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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6148 Midnight Pass Rd

— Property 62204h
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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Island House Beach Resort

— Property 62205h
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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6150 Midnight Pass Rd

— Property 62160h
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 62214h
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 62211h
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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Siesta Gardens #4

— Property 72072h
Siesta Key villa rental
1 Bedroom, Sleeps 2,
Villa, 1 Bathroom, adventure, balcony
Rates - per villa (USD)
$125 - $165/night
$650 - $1,000/week
$1,250 - $2,800/month
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Luxury Condo, Direct Beachfront, Phenomenal Views of Siesta Key Beach

— Property 247524
Siesta Key condo rental - View from every room
2 Bedrooms, Sleeps 6,
Condo, 2 Bathrooms, beach, waterfront, pool
Rates - per property (USD)
$1,665 - $1,885/week
Calendar Updated Nov 12 2009

Property Review

We had a wonderful time in this condo. It has a special location with full view of the crescent beach from the top floor of Crystal Sands condominium. The condo was nicely decorated and there was...
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Gulf view & steps from beach and village - luxury Townhouse - FALL SPECIAL

— 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)
$1,290 - $2,190/week
$4,000 - $6,800/month
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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 Nov 12 2009

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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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 12 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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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
$195 - $1,795/week
Calendar Updated Nov 13 2009

Property Review

We hope to come back in the future. We had a lovely time!
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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 13 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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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