Vacation Rentals in Siesta Key, Sarasota

Condo Rental 4.9 Star Review

Siesta Key, Florida
2 Bedrooms 2 Bath(s) Sleeps 6

Siesta Key - Beachfront Condo - 2 BR – Free Boat Docks - Upscale - Renovated

Private Home Rental 5.0 Star Review

Siesta Key, Florida
4 Bedrooms 6 Bath(s) Sleeps 8

Luxurious Waterfront Retreat minutes from Beach, bay front with city views.

Condo Rental 5.0 Star Review

Siesta Key, Florida
2 Bedrooms 2 Bath(s) Sleeps 4

4th Floor Crescent Beach Condo Offering Full Unobstructed Gulf Views.

Condo Rental 5.0 Star Review

Siesta Key, Florida
2 Bedrooms 2 Bath(s) Sleeps 6

Firethorn 611 - 2 Bedroom Condo with Private Beach with lounge chairs & umbrella provided, 2 Pool...

Condo Rental 4.8 Star Review

Siesta Key, Florida
2 Bedrooms 2 Bath(s) Sleeps 4

Luxury on Crescent Beach - Great Location!

Apartment Rental 4.9 Star Review

Siesta Key, Florida
2 Bedrooms 2 Bath(s) Sleeps 5

Walk To Siesta Village And Beach/Private Pool & Hot Tub

Condo Rental 4.9 Star Review

Siesta Key, Florida
3 Bedrooms 2 Bath(s) Sleeps 8

BEACHFRONT CONDO - THREE BEDROOM - HEATED POOL - FREE BOAT DOCKS - RENOVATED

Condo Rental 3.9 Star Review

Siesta Key, Florida
2 Bedrooms 2 Bath(s) Sleeps 6

Ground Floor at Bay Oaks in Siesta Key - Watch Dolphin in the Bay - Fish from the Pier. Unit E81

Condo Rental 4.5 Star Review

Siesta Key, Florida
2 Bedrooms 2 Bath(s) Sleeps 6

Sprinkle of Irish charm, beautifully updated, Siesta Dunes 8-205

Condo Rental 5.0 Star Review

Siesta Key, Florida
2 Bedrooms 2 Bath(s) Sleeps 5

1st Floor Gulf View, Convenient Walk Out to Pool w/ 3 Porches!

Apartment Rental 5.0 Star Review

Siesta Key, Florida
3 Bedrooms 3 Bath(s) Sleeps 9

Stunning 3 Bedroom Home with Roof-Top Pool on Siesta Key!

Private Home Rental

Siesta Key, Florida
3 Bedrooms 3 Bath(s) Sleeps 8

Stunning 3 bed/ 2.5 bath Townhouse Steps From Siesta Key Beach!

Condo Rental 4.3 Star Review

Siesta Key, Florida
2 Bedrooms 2 Bath(s) Sleeps 6

Beautiful 2Bed/2Bath at Crystal Sands, Steps from Pool and Siesta Key Beach!!

Apartment Rental 5.0 Star Review

Siesta Key, Florida
3 Bedrooms 3 Bath(s) Sleeps 9

Beautiful 3 Bed/2.5 bath With Roof Top Pool on Siesta Key!

Private Home Rental 4.9 Star Review

Siesta Key, Florida
2 Bedrooms 2 Bath(s) Sleeps 6

Prime Location! 200 feet to the beach. 2 blocks to shopping and restaurants

Private Home Rental

Siesta Key, Florida
4 Bedrooms 3 Bath(s) Sleeps 8

NEW! Luxury 4/3 Home on Siesta Key w. Heated Pool & Water View!

Condo Rental 5.0 Star Review

Siesta Key, Florida
3 Bedrooms 3 Bath(s) Sleeps 8

Modern 3 Bed/2.5 bath Gulf Side Condo Steps from Siesta Key Village and Beach!!

Condo Rental 3.7 Star Review

Siesta Key, Florida
2 Bedrooms 2 Bath(s) Sleeps 5

Updated Top Floor Siesta Key Vacation Rental at Bay Oaks

Condo Rental 5.0 Star Review

Siesta Key, Florida
2 Bedrooms 2 Bath(s) Sleeps 8

Beautifully Updated Ground Floor at Gulf & Bay Club. Gulf Front Living at it's Finest!

Condo Rental 4.8 Star Review

Siesta Key, Florida
2 Bedrooms 2 Bath(s) Sleeps 5

Bay Oaks, End Unit, Walk to Beach, WiFi, Updated, Pool, Tennis, Complex Fishing Pier

Condo Rental 4.0 Star Review

Siesta Key, Florida
2 Bedrooms 2 Bath(s) Sleeps 4

New Listing! Ground floor, easy access to the pool and beach! Siesta Dunes 2-104

Private Home Rental 4.8 Star Review

Siesta Key, Florida
3 Bedrooms 3 Bath(s) Sleeps 6

Perfect Siesta Village Pool Home! Walk to the beach and hang out in the Village!

Condo Rental 5.0 Star Review

Siesta Key, Florida
Studio 1 Bath(s) Sleeps 2

Cozy Siesta Key studio 5 minute walk to Village

Condo Rental 4.9 Star Review

Siesta Key, Florida
1 Bedrooms 1 Bath(s) Sleeps 4

Cozy Romantic Siesta Key Beachfront Condo-full beach view. 50 steps to the beach

Cottage Rental 4.8 Star Review

Siesta Key, Florida
2 Bedrooms 2 Bath(s) Sleeps 4

Prem 2Bed/2Bath Gate House Cottage with private beach access!

Private Home Rental 5.0 Star Review

Siesta Key, Florida
3 Bedrooms 2 Bath(s) Sleeps 8

3 bedroom house+ Private pool + huge yard. 12min walk to beach. Pet friendly.

Condo Rental 4.8 Star Review

Siesta Key, Florida
2 Bedrooms 2 Bath(s) Sleeps 6

Bay, Pool, Tennis Court Views, 2 Master Suites, Stainless Kitchen, Tile Floors, 3 TV's

Condo Rental 4.8 Star Review

Siesta Key, Florida
2 Bedrooms 2 Bath(s) Sleeps 6

NEWLY REMODELED! On World Famous Crescent Beach

Condo Rental

Siesta Key, Florida
2 Bedrooms 2 Bath(s) Sleeps 6

Stunning Siesta Key Beach Views from 2 Bedroom Condo!!

Private Home Rental 2.5 Star Review

Siesta Key, Florida
3 Bedrooms 3 Bath(s) Sleeps 8

Spacious 3 Bedroom Gulf Side Townhome with Rooftop Sun Deck On Siesta Key!!

Condo Rental 4.6 Star Review

Siesta Key, Florida
2 Bedrooms 2 Bath(s) Sleeps 6

SIESTA KEY! MIDNIGHT COVE 2/2 GULFRONT! BOOKING FOR SUMMER/FALL 2023 NOW!

Apartment Rental

Siesta Key, Florida
2 Bedrooms 2 Bath(s) Sleeps 4

2 Bedroom Single_family (427377) by Houzlet

Private Home Rental 3.0 Star Review

Siesta Key, Florida
3 Bedrooms 3 Bath(s) Sleeps 6

Beautiful 3 Bedroom Home With Rooftop Sun Deck & Views of Siesta Key Beach!

Condo Rental 5.0 Star Review

Siesta Key, Florida
3 Bedrooms 2 Bath(s) Sleeps 6

Buttonwood 447 - 3 Bedroom Condo with Private Beach with lounge chairs & umbrella provided, 2 Poo...

Condo Rental

Siesta Key, Florida
2 Bedrooms 2 Bath(s) Sleeps 4

NEW LISTING! Spend your winter in this condo just steps from Siesta Village!

Private Home Rental

Siesta Key, Florida
4 Bedrooms 4 Bath(s) Sleeps 12

Beautiful 4 Bedroom/ 4 Bath Beach House-Directly on Beach!

Condo Rental 3.0 Star Review

Siesta Key, Florida
2 Bedrooms 2 Bath(s) Sleeps 6

Chinaberry 413 - 2 Bedroom Condo with Private Beach with lounge chairs & umbrella provided, 2 Poo...

Condo Rental

Siesta Key, Florida
3 Bedrooms 2 Bath(s) Sleeps 6

Buttonwood 940 - 3 Bedroom Condo with Private Beach with lounge chairs & umbrella provided, 2 Poo...

Condo Rental 5.0 Star Review

Siesta Key, Florida
3 Bedrooms 2 Bath(s) Sleeps 6

Buttonwood 472 - 3 Bedroom Condo with Private Beach with lounge chairs & umbrella provided, 2 Poo...

Condo Rental 5.0 Star Review

Siesta Key, Florida
2 Bedrooms 2 Bath(s) Sleeps 6

Chinaberry 414 - 2 Bedroom Condo with Private Beach with lounge chairs & umbrella provided, 2 Poo...

Condo Rental

Siesta Key, Florida
3 Bedrooms 2 Bath(s) Sleeps 6

Buttonwood 950 - 3 Bedroom Condo with Private Beach with lounge chairs & umbrella provided, 2 Poo...

Condo Rental 4.0 Star Review

Siesta Key, Florida
2 Bedrooms 2 Bath(s) Sleeps 6

Chinaberry 423 - 2 Bedroom Condo with Private Beach with lounge chairs & umbrella provided, 2 Poo...

Condo Rental 4.9 Star Review

Siesta Key, Florida
1 Bedrooms 1 Bath(s) Sleeps 4

NOV and DEC AVAILABLE!! 1 bedroom 1 bathroom with access to private beach

Private Home Rental 4.8 Star Review

Siesta Key, Florida
3 Bedrooms 3 Bath(s) Sleeps 8

Grand Canal Front 3BR/3bath, Pool/Hot Tub, Walk to Beach & Siesta Village

Condo Rental 4.7 Star Review

Siesta Key, Florida
2 Bedrooms 2 Bath(s) Sleeps 6

Chinaberry 456 - 2 Bedroom Condo with Private Beach with lounge chairs & umbrella provided, 2 Poo...

Condo Rental 5.0 Star Review

Siesta Key, Florida
3 Bedrooms 2 Bath(s) Sleeps 6

Buttonwood 417 - 3 Bedroom Condo with Private Beach with lounge chairs & umbrella provided, 2 Poo...

Condo Rental 5.0 Star Review

Siesta Key, Florida
2 Bedrooms 2 Bath(s) Sleeps 6

Chinaberry 913 - 2 Bedroom Condo with Private Beach with lounge chairs & umbrella provided, 2 Poo...

Condo Rental 5.0 Star Review

Siesta Key, Florida
2 Bedrooms 2 Bath(s) Sleeps 4

Peppertree Bay Gulf Beach!- Steps from your private beach

Apartment Rental 4.0 Star Review

Siesta Key, Florida
5 Bedrooms 5 Bath(s) Sleeps 11

Luxury 5 Bed with Stunning Siesta Key Beach Views!

Condo Rental 3.8 Star Review

Siesta Key, Florida
2 Bedrooms 2 Bath(s) Sleeps 4

Waterfront Condo at The Inlet - Great Views, Heated Pool on the Bay Quiet, Friendly Community #39

Condo Rental 4.8 Star Review

Siesta Key, Florida
1 Bedrooms 1 Bath(s) Sleeps 4

COZY UNIT ON THE BEACH ACCESS TO 3 POOLS

Private Home Rental 4.9 Star Review

Siesta Key, Florida
3 Bedrooms 5 Bath(s) Sleeps 8

5 Star LUXURY RETREAT on BEACH ROAD, SIESTA KEY BEACH, New POOL

Condo Rental 4.9 Star Review

Siesta key, Florida
2 Bedrooms 2 Bath(s) Sleeps 6

Crescent Siesta Key #406 Luxury Property

Condo Rental 5.0 Star Review

Siesta Key, Florida
2 Bedrooms 4 Bath(s) Sleeps 6

Newly renovated Siesta Key 2br 3.5 bath condo! 1800 sq ft. #1 beach in the USA!

Cottage Rental 5.0 Star Review

Siesta Key, Florida
1 Bedrooms 1 Bath(s) Sleeps 2

Key West style beach cottage JUST STEPS from #1 SIESTA KEY BEACH!

Villa Rental 5.0 Star Review

Siesta Key, Florida
2 Bedrooms 2 Bath(s) Sleeps 6

Updated Villa with Beach and Heated Pool

Private Home Rental 5.0 Star Review

Siesta Key, Florida
4 Bedrooms 3 Bath(s) Sleeps 10

Walk to Siesta Key beach. Large heated pool and hot tub. Nature at its best!

Private Home Rental 4.9 Star Review

Siesta Key, Florida
3 Bedrooms 3 Bath(s) Sleeps 6

Waterfront/Pool Home under 5 min walk to Siesta Key Village and Beach

Condo Rental 3.0 Star Review

Siesta Key, Florida
3 Bedrooms 3 Bath(s) Sleeps 8

A Gem in Siesta Key FL - #1 beach in US

Private Home Rental

Siesta Key, Florida
5 Bedrooms 4 Bath(s) Sleeps 14

Beautiful 5 Bedroom Home Directly on Siesta Key Beach!!