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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FLASH SALE! Left to Save 28% 4/27 - 5/4!

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.
Was $864.81
NOW $624.73

FLASH SALE! Left to Save 28% 4/27 - 5/4!

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 ...
Was $1,116.71
NOW $806.71

FLASH SALE! Left to Save 28% 4/27 - 5/11!

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

Excelsior, Siesta Key, FL
3 BR, 2 BA, Sleeps 6,Pool View
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!
Was $2,228.80
NOW $1,610.06

FLASH SALE! Left to Save 28% 4/27 - 5/4!

Anchorage 904, 2 Bedrooms, Gorgeous Views, WIFI, Pool, Sauna, Sleeps 6

Sarasota, FL
2 BR, 2 BA, Sleeps 6,Gulf View
You’ll be living the high life at Anchorage 904—literally and figuratively. Located on the 9th floor of the Anchorage Yacht & Tennis Club, the 2-bedroom condo offers panoramic views of the Gulf of Mexico, Siesta Key & beyond.
Was $874.72
NOW $631.89

FLASH SALE! Left to Save 28% 4/27 - 5/11!

White Sands Village 205, 2 Bedrooms, Heated Pool, WIFI, Sleeps 6

White Sands Village, Siesta Key, FL
2 BR, 2 BA, Sleeps 6,Best Value/Garden
Beat a path to the beach every day from your own breezy lanai when you stay at this ground-floor condo in a lovely resort. The latest technology, comfy furnishings, and the perfect location await you!
Was $1,270.08
NOW $917.48

FLASH SALE! Left to Save 28% 4/27 - 5/4!

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.
Was $1,280.85
NOW $925.28

FLASH SALE! Left to Save 28% 4/27 - 5/4!

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 $714.98
NOW $516.49

FLASH SALE! Left to Save 28% 4/27 - 5/4!

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
Just steps from the bay, our newly 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 $1,890
NOW $1,365.33

FLASH SALE! Left to Save 28% 4/27 - 5/4!

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 ...
Only 3 weeks left in the next 60 days!
Was $714.98
NOW $516.49

FLASH SALE! Left to Save 28% 4/27 - 5/4!

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

Anchorage, Sarasota, FL
2 BR, 2 BA, Sleeps 6,Water View
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.
Only 3 weeks left in the next 60 days!
Was $794.85
NOW $574.19

FLASH SALE! Left to Save 28% 4/27 - 5/4!

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

Sarasota, FL
3 BR, 2 BA, Sleeps 8,Gulf View
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.
Was $1,274.14
NOW $920.43

Limited-Time Offer: Stay before 6/15/19 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
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 NOW!

Limited-Time Offer: Stay before 6/15/19 and Save Up to 28%!

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.
ONLY $300 TO BOOK NOW!

Limited-Time Offer: Stay before 6/15/19 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
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 $300 TO BOOK NOW!

Limited-Time Offer: Stay before 6/15/19 and Save Up to 28%!

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 NOW!

Limited-Time Offer: Stay before 6/15/19 and Save Up to 28%!

Siesta Shores B13, 3 Bedrooms, 2 Bathroom, Pet Friendly, Sleeps 8

Sarasota, FL
3 BR, 2 BA, Sleeps 8,Best Value/Garden
Situated just steps away from the "world's finest, whitest sand" and all of the enjoyment that Siesta Key has to offer, this lovely three bedroom/two bathroom cottage sleeps eight guests and is the perfect Floridian escape for your next ...
Only 1 week left in the next 60 days!
ONLY $300 TO BOOK NOW!

Limited-Time Offer: Stay before 6/15/19 and Save Up to 28%!

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
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 2 weeks left in the next 60 days!
ONLY $300 TO BOOK NOW!

Limited-Time Offer: Stay before 6/15/19 and Save Up to 28%!

Gulf and Bay Club 305C , Sleeps 6, 3 pools, Gulf and Bay Club 305C, 2 Bedrooms, Gym, WiFi,

Gulf & Bay Club, Siesta Key, FL
2 BR, 2 BA, Sleeps 6,Gulf View
Roll into the lap of luxury and enjoy a unit that’s still sparkling new. Siesta Key Gulf and Bay Club is known to be the finest long-stay resort in the area - and this newly renovated unit with a new air conditioning and heating system, Gulf and Bay Club ...
ONLY $300 TO BOOK NOW!

Limited-Time Offer: Stay before 6/15/19 and Save Up to 28%!

Bay Tree Club 106, 2 Heated Pools, 2 Bedrooms, Spa, WiFi, Sleeps 6

Bay Tree Club, Siesta Key, FL
2 BR, 2 BA, Sleeps 6,Beach Front
With the Gulf of Mexico just steps from your back door and beautiful Sarasota Bay a couple minutes’ drive in the other direction, Bay Tree Club 106 is perfectly situated for fun on Siesta Key. In 2011 Siesta Beach was named the Best Beach in America.
Only 2 weeks left in the next 60 days!
ONLY $300 TO BOOK NOW!

Limited-Time Offer: Stay before 6/15/19 and Save Up to 28%!

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 NOW!

Limited-Time Offer: Stay before 6/15/19 and Save Up to 28%!

Siesta Dunes Beach 201, COMPLETE RENOVATION FALL 2017, 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 in the fall of 2017. Stunning seaside decor, new kitchen, baths, paint, and luxury vinyl plank flooring throughout.
Only 1 week left in the next 60 days!
ONLY $300 TO BOOK NOW!