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SHOWING: 15 Listings
(in $USD per week)
Southwest Florida Vacation Rentals:
SIESTA KEY
Florida's Siesta Key has one of the top 10 beaches on Earth! This island gem lies between the Bay and the Gulf of Mexico - enjoy beautiful sunsets nightly. No car needed; ride vacationer-friendly trolleys. Choose one of our oceanfront condos steps from the Gulf. Excellent values with full furnishings, amenities.
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Vista Hermosa 189, Wireless Internet, 2 Bedrooms, Pool, Sleeps 6

Sarasota, FL
2 BR, 2 BA, Sleeps 6,Resort View
When booking a Florida rental for a stay of at least two weeks, you want a place that has it all: a convenient location, comfortable and attractive furnishings, and amenities such as a swimming pool, free WiFi, and a private washer and dryer. Vista Hermosa ...
ONLY $300 TO BOOK*

Beachaven 52, Sleeps 4, Ground Floor, 1 Bedroom, Pool

Beach Haven, Siesta Key, FL
1 BR, 2 BA, Sleeps 4,Best Value/Garden
Imagine this: You step out your front door, and there, at the end of a walkway flanked by shrubbery on one side and an impeccably manicured lawn. On the other, are the twinkling white sands of Crescent Beach and just beyond, the sparkling Gulf of Mexico.
ONLY $300 TO BOOK*

Our House at the Beach 222, Sleeps 4, 2 Bedroom, Tennis, Heated Pool

Siesta Key, FL
2 BR, 2 BA, Sleeps 4,Lake View
There's plenty of room for everyone here at Our House. We have a split-level living/dining area, with a large living room made for a crowd!
ONLY $300 TO BOOK*

Village des Pins 3645, 2 Bedrooms, Pool Access, WiFi, Hot Tub, Sleeps 4

Sarasota, FL
2 BR, 2 BA, Sleeps 4,Best Value/Garden
At Village des Pins 3645 you’ll be able to experience all the joys of the Florida lifestyle. Strolling among the lushly landscaped grounds in the quiet cool of the morning, playing tennis on the complex’s courts,or taking a dip in the heated pool whenever you ...
ONLY $300 TO BOOK*

Siesta Dunes Beach 201, Completely Renovated, 2 Bedrooms, Sleeps 6, Spa, Large Heated Pool, WiFi

Siesta Dunes, Siesta Key, FL
2 BR, 2 BA, Sleeps 6,Best Value/Garden
This unit has been newly renovated. Stunning seaside decor, new kitchen, baths, paint, and luxury vinyl plank flooring throughout.
ONLY $300 TO BOOK*

Jamaica Royale 91, 3 Heated Pools, 2 Bedrooms, WiFi, Sleeps 6

Jamaica Royale, Siesta Key, FL
2 BR, 2 BA, Sleeps 6,Best Value/Garden
In this handy ground-floor condo, you're just a short walk away from gorgeous Crescent Beach, the jewel in Siesta Key's crown. Enjoy laid-back beach living, from the open-air patio to the sun-washed living room!
Only 2 weeks left in the next 60 days!
ONLY $300 TO BOOK*

Crescent Street 1138 B, Walk to the beach, Pool, 1 Bedroom, Pet Friendly

Point of Rocks, Siesta Key, FL
1 BR, 1 BA, Sleeps 4,Best Value/Garden
Half-hidden by lush tropical foliage, Crescent Street 1138 B is paradise for anyone who longs to relax in time-honored Florida style. Just a few blocks from Siesta Key’s quartz-white beach and the renowned Point of Rocks, the pet-friendly home is a haven in ...
Only 1 week left in the next 60 days!
ONLY $300 TO BOOK*

Gulf and Bay Club 108D, Sleeps 4, Beach Front, Ground Floor, 2 Bedroom

Gulf & Bay Club, Siesta Key, FL
2 BR, 2 BA, Sleeps 4,Beach Front
Get away from everyday life and enjoy a month alongside the #1 beach in the USA; Gulf and Bay Club 108D is just what you are looking to find. This garden level condo is part of a resort that offers you endless entertainment possibilities plus the condo itself ...
ONLY $300 TO BOOK*

Jamaica Royale 101, 2 Bedrooms, 3 Heated Pools, WiFi, Sleeps 6

Jamaica Royale, Siesta Key, FL
2 BR, 2 BA, Sleeps 6,Best Value/Garden
Enjoy an amazing location and luxurious accommodations! With indoor and outdoor seating, three heated pools, and a short walk to the sandy beach, your family will have the vacation of a lifetime here!
Only 2 weeks left in the next 60 days!
ONLY $300 TO BOOK*

Gulf and Bay Club 204C, Beach Front, Spa, 3 Pools, Sleeps 6, 2 Bedroom, Gym

Gulf & Bay Club, Siesta Key, FL
2 BR, 2 BA, Sleeps 6,Gulf View
Come vacation on the white sands of Siesta Beach! When you stay at our condo at Gulf and Bay Club 204C, you'll enjoy luxury and comfort in more than 1,500 sq ft of beachfront property, including a lovely lanai.
Only 3 weeks left in the next 60 days!
ONLY $300 TO BOOK*

Crescent Street 1138 A, pet-friendly, 2 bedrooms, Pool, Walk to the beach

Point of Rocks, Siesta Key, FL
2 BR, 1 BA, Sleeps 6,Best Value/Garden
When you stay at Crescent Street 1138A, you can walk to the east side of Siesta Key in just minutes to catch the sunrise over the Gulf of Mexico. Then later, just before dusk, you can take an equally brief stroll over to the west side of the barrier island to ...
Only 1 week left in the next 60 days!
ONLY $300 TO BOOK*

Crescent Street Manor, 3 Bedrooms, Private Pool, Sleeps 10, Walk to Beach

Point of Rocks, Siesta Key, FL
3 BR, 2 BA, Sleeps 10,Best Value/Garden
When you stay at Crescent Street Manor, you can walk to the east side of Siesta Key in just minutes to catch the sunrise over the Gulf of Mexico. Then later, just before dusk, you can take a stroll over to the west side of the barrier island to watch the ...
Only 1 week left in the next 60 days!
ONLY $300 TO BOOK*

Gulf and Bay Club 102B, Sleeps 4, Lagoon View, Ground Floor, 2 Bedrooms

Gulf & Bay Club, Siesta Key, FL
2 BR, 2 BA, Sleeps 6,Lagoon View
Ready to spend twenty-eight days or more in paradise? If so, Gulf & Bay Club 102B is waiting for you.
ONLY $300 TO BOOK*

Siesta Chillin Anchorage 305, 2 Bedrooms, Pool Access, Boat Dock, WiFi, Sleeps 6

Anchorage, Sarasota, FL
2 BR, 2 BA, Sleeps 6,Water View
We invite you to stay in our spacious 2 bed 2 bath condo, 'Siesta Chillin', across from the beautiful crystal sands of Crescent Beach on Siesta Key. Siesta Chillin has been recently updated and has all the conveniences of home in an amazing vacation ...
ONLY $300 TO BOOK*

Anchorage 909, 2 Bedrooms, Private Beach Access, Boat Dock, WIFI, Sleeps 6

Sarasota, FL
2 BR, 2 BA, Sleeps 6,Bay View
Breathtaking, panoramic views await you at this luxurious penthouse condo on the 9th floor of an elevator building overlooking the Intracoastal Waterway! Enjoy 200+ sq ft of balcony bliss!
Only 2 weeks left in the next 60 days!
ONLY $300 TO BOOK*

If your reservation is within 45 days, full payment is required. A reservation deposit of $300 is required for amounts up to $1,000. A deposit of $1,000 for booking amounts $4,000 and up is required. All deposits must be paid at the time of booking. The deposit is applied toward the total amount due and is only refundable within 48 hours of booking. CANCELLATIONS: After 48 hours of booking, if canceled, or in case of no-show, the total amount of the reservation will be charged.