Siesta Keyholiday rentals

From simple studios to luxe lofts, find holiday rentals that are right for you on Airbnb.
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Holiday rentals in Siesta Key

$254 AUD Beachfront Getaway in Siesta Key
68 reviews

Beachfront complex, this gorgeous home boasts all the luxury you’d expect from a beach house! Beachfront BBQ grills, cabana with lounge chairs,heated swimming pool, Wi-Fi & park... read more
$216 AUD 150 yds to Crescent Beach & Pool!
85 reviews

A delightfully cool and comfortable 2 bed villa on tropical Siesta Key. It comfortably fits 4 and is conveniently located just 150 yards from the famous Crescent Beach. Enjoy dr... read more
$445 AUD Siesta Key Waterfront Fishing Shack
18 reviews

Charming waterfront cottage with a hot tub, tiki hut and beach at the end of the street. Located on one of the best streets on Siesta Key. Betty Davis frequently visited and s... read more
$216 AUD 150 yds to Siesta Key Beach & Pool!
48 reviews

A delightfully cool and comfortable 2 bed villa on the tropical Siesta Key. It comfortably fits 4 and is conveniently located just 150 yards from the famous Crescent Beach. Enjo... read more
$270 AUD Siesta Beach House
24 reviews

This Pool/Home is literally less than 200 feet from world famous Siesta Beach. This 60+ year old beach house has been remodeled in 2015. This 2BR/1B house features a front porc... read more
$127 AUD Best of both worlds on Siesta Key!
21 reviews

1st floor 1br condo on the bay side. Fish off the dock, swim in the pool, then walk across the street and enjoy the pristine white sand of Siesta Key. The condo has it's own wi... read more

Favourite Siesta Key holiday rentals

$203 AUD Siesta Key Beach Artist Hideaway BB
72 reviews

Location, location, location! Our peaceful Island home faces Siesta Key's Grand Canal and is only 4 blocks from USA's #1 Beach & SK Village shops & dining. Enchanting art, priva... read more
$369 AUD Siesta Key leisurely perfection
38 reviews

Your vacation home is directly on Siesta Key's Crescent Beach with powdery white sand that stretches for miles. Overlooking the action is your large, clean home with views of th... read more
$162 AUD Delightful, cozy Siesta Key Cottage! Ebb Tide #2
46 reviews

If you're looking for a clean, comfortable, updated place to call your own for your vacation stay at the beach, you've found it! This comfortable cottage offers everything you n... read more
$226 AUD Sunspot Cottage your 2BR/2B Getaway
60 reviews

Stay at our newly renovated open and relaxing vacation rental... Welcome to Sunspot at Sea Club II located on the Intracoastal Waterways and across the street from the world fam... read more
$155 AUD Siesta Key Studio near beach & pool
84 reviews

A delightfully cool and comfortable studio on the tropical Siesta Key. It comfortably fits two and is conveniently located just 150 yards from the famous Crescent Beach. Enjoy c... read more
$228 AUD Cute Siesta Key Cottage! Renovated!
52 reviews

Charming Siesta Cottage, 2/1, queen, 2 twin. Located between Access 9 and 10 across street from beach. Full yard, pet friendly! Fully renovated. Bikes, beach chairs, umbrell... read more

More holiday rentals in Siesta Key

$182 AUD Come to the Sea and Stay on the Key!
32 reviews

Welcome to our one bedroom, one bath (4 piece) main floor condo. Easily accessible with no steps to climb and close, convenient parking right outside the front door. Quiet, peac... read more
$162 AUD Bright, cozy, Siesta Key cottage! Ebb Tide #1
45 reviews

This charming, cottage-style condo offers all you need for a fun and relaxing vacation at the beach. The white, quartz sands of Crescent Beach on Siesta Key are just 3 minute wa... read more
$155 AUD Siesta Key ~ Sarasota ~ Condo
28 reviews

Welcome to our Condo in Siesta Key ! Located on the intercoastal Waterway and a short walk to the whitest sand and the # 1 beach in America. This 1 bedroom Condo is a great re... read more
$269 AUD 60 Steps to Sand - 3bedroom 2bath
40 reviews

60 Steps to Sand perfectly positioned between Siesta Key Village & Public Beach. Just 60 steps across the beach road puts your feet in sand. 4 blocks north to the village make d... read more

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