SIESTA KEY VACATION RENTALS
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FLASH SALE! Left to Save 28% 10/26 - 11/2 or Save 28% 10/19 - 10/26!

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

Beach Haven, Siesta Key, FL
1 BR, 2 BA, Sleeps 4,Best Value/Garden
Guest Ratings: 4.5/5 (5)
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.
Was $840.14
NOW $606.91

FLASH SALE! Left to Save 28% 10/26 - 11/2 or Save 28% 10/19 - 10/26!

Inlet 21, Renovated 2 Bedroom, Lagoon and Gulf Views, Pool, WiFi, Sleeps 6

Sarasota, FL
2 BR, 2 BA, Sleeps 6,Gulf View
Are you ready for a great escape? If so, Inlet 21 is the perfect spot for you.
Was $840.14
NOW $606.91

FLASH SALE! Left to Save 28% 10/26 - 11/2 or Save 28% 10/19 - 10/26!

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

Anchorage, Sarasota, FL
2 BR, 2 BA, Sleeps 6,Water View
Guest Ratings: 5/5 (1)
You’ll enjoy beautiful views when you vacation at Siesta Chillin Anchorage 305 in beautiful Siesta Key, Florida. Up to six friends or family members will experience the pleasures of what has been named “the best beach in the US.
Was $841.61
NOW $607.97

FLASH SALE! Left to Save 28% 10/19 - 11/2!

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 ...
Was $1,852.48
NOW $1,338.22

FLASH SALE! Left to Save 28% 10/19 - 10/26 or Save 28% 10/26 - 11/2!

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
Guest Ratings: 4/5 (2)
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.
Was $1,063.16
NOW $768.02

FLASH SALE! Left to Save 28% 10/26 - 11/2 or Save 28% 10/19 - 10/26!

Gulf and Bay Club: Bayside 1226, Ground Floor, Sleeps 6, 2 Bedrooms, 2 Pools, Gym

Gulf & Bay Club, Siesta Key, FL
2 BR, 2 BA, Sleeps 6,Best Value/Garden
Guest Ratings: 4.5/5 (21)
Just steps from the beach & bay, our remodeled condo in a gated Key West-style community is the perfect destination for your Siesta Key vacation. With resort amenities and the ideal location for beach and bay access, Gulf and Bay Bayside is irresistible!
Was $1,149.96
NOW $830.72

FLASH SALE! Left to Save 28% 10/26 - 11/2!

Gulf and Bay Club 102B, Sleeps 4, Beach Front, Ground Floor, 2 Bedrooms

Gulf & Bay Club, Siesta Key, FL
2 BR, 2 BA, Sleeps 6,Beach Front
Guest Ratings: 5/5 (1)
Ready to spend twenty-eight days or more in paradise? If so, Gulf & Bay Club 102B is waiting for you.
Was $877.53
NOW $633.92

FLASH SALE! Left to Save 28% 10/26 - 11/2 or Save 28% 10/19 - 10/26!

Gulf and Bay Club: Bayside 1303-D, Sleeps 6, 2 Bedrooms, 2 Pools, Gym

Gulf & Bay Club, Siesta Key, FL
2 BR, 2 BA, Sleeps 6,Best Value/Garden, Free Wifi
Experience Siesta Key from Bayside 1303-D and get ready for the perfect vacation! This beautiful condo features two accommodating bedrooms, two bathrooms and sleeps six.
Was $1,149.96
NOW $830.72

FLASH SALE! Left to Save 28% 10/19 - 10/26!

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
Guest Ratings: 4.5/5 (18)
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 ...
Was $671.65
NOW $485.19

FLASH SALE! Left to Save 28% 10/26 - 11/2 or Save 28% 10/19 - 10/26!

Polynesian Gardens Villa P6, Carport, 2 Bedrooms, Heated Pool

Polynesian Gardens, Siesta Key, FL
2 BR, 2 BA, Sleeps 4,Best Value/Garden
Guest Ratings: 5/5 (1)
Welcome to your home in paradise; This standalone two -bedroom villa offers privacy and relaxation for an incredible family vacation. Come and experience this tropical retreat by the Siesta Key beaches!
Was $926.24
NOW $669.11

FLASH SALE! Left to Save 28% 10/19 - 10/26!

Gulf Holidays 15, Sleeps 4, 2nd Floor, 1 Bedroom, Heated Pool

Gulf Holidays, Siesta Key, FL
1 BR, 1 BA, Sleeps 4,Best Value/Garden
Budget-friendly and just a block from a beach rated #1 in the country, it’s easy to see why Gulf Holidays 15 is a very popular place to vacation in beautiful Siesta Key. Gulf Holidays 15 is one of just eighteen condos in the community that offers a beautiful ...
Was $757.05
NOW $546.89

FLASH SALE! Left to Save 28% 10/19 - 10/26!

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

Siesta Key, FL
2 BR, 2 BA, Sleeps 4,Lake View
Guest Ratings: 4.5/5 (45)
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!
Was $1,281.14
NOW $925.48

FLASH SALE! Left to Save 28% 10/26 - 11/2!

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
Guest Ratings: 4.5/5 (7)
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 3 weeks left in the next 60 days!
Was $841.61
NOW $607.97

FLASH SALE! Left to Save 28% 10/19 - 10/26!

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 2 weeks left in the next 60 days!
Was $826.91
NOW $597.35

FLASH SALE! Left to Save 28% 10/26 - 11/2 or Save 28% 10/19 - 10/26!

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
Guest Ratings: 4.5/5 (27)
This unit has been newly renovated. Stunning seaside decor, new kitchen, baths, paint, and luxury vinyl plank flooring throughout.
Was $1,010.73
NOW $730.14

Limited-Time Offer: Stay before 12/14/19 and Save Up to 28%!

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

Sarasota, FL
2 BR, 2 BA, Sleeps 4,Best Value/Garden
Guest Ratings: 5/5 (1)
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!

Limited-Time Offer: Stay before 12/14/19 and Save Up to 28%!

Siesta Key Excelsior 306, Sleeps 6, 3 Bedrooms, Tennis, Pools

Excelsior, Siesta Key, FL
3 BR, 2 BA, Sleeps 6,Pool View
Guest Ratings: 5/5 (1)
With spectacular views of the beautiful trees, pond, pool, and peek a boo view of the Intracoastal, you will be asking yourself why you didn't choose Excelsior 306 sooner. Our three bedroom condo sits on a little strip of paradise!
ONLY $300 TO BOOK!

Limited-Time Offer: Stay before 12/14/19 and Save Up to 28%!

Palm Bay Club G34, 1 Bedroom, Heated Pool, WiFi, Hot Tub, Sleeps 4

Palm Bay Club, Siesta Key, FL
1 BR, 1 BA, Sleeps 4,Gulf View
Guest Ratings: 4.5/5 (4)
Both TripAdvisor and Dr. Beach named Siesta Beach the country’s best beach.
ONLY $300 TO BOOK!

Limited-Time Offer: Stay before 12/14/19 and Save Up to 28%!

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

Sarasota, FL
2 BR, 2 BA, Sleeps 6,Bay View
Guest Ratings: 5/5 (6)
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 3 weeks left in the next 60 days!
ONLY $300 TO BOOK!

Limited-Time Offer: Stay before 12/14/19 and Save Up to 28%!

Beach Walk Unit B, 3 Bedrooms, Pool Access, WiFi, Sleeps 8

Sarasota, FL
3 BR, 2 BA, Sleeps 8,Gulf View
Guest Ratings: 5/5 (9)
Experience Siesta Key from Beach Walk Unit B and enjoy the beautiful gulf view! This condo features three accommodating bedrooms, two-and-a-half bathrooms, and sleeps eight.
ONLY $300 TO BOOK!

Palm Bay Club G46, Sleeps 4, 1 Bedroom, Heated Pool, 40" HDTV, WiFi

Palm Bay Club, Siesta Key, FL
1 BR, 1 BA, Sleeps 4,Best Value/Garden
Guest Ratings: 4.5/5 (58)
With the top-rated beach in the country in your backyard, Palm Bay Club G46 delivers the perfect vacation. Just take an elevator ride down from your fourth-floor condo and you’ll be right at the beach, ready to sink your toes into warm silky sands and ...
Only 3 weeks left in the next 60 days!
ONLY $300 TO BOOK!