Where To Stay
Our island is small but your accommodation options are abundant. On Siesta Key you’ll find old Florida-style beach resorts nestled among palms, large vacation homes overlooking the bay, beachfront condos that sleep two to twelve, boutique bungalows steps from the Gulf of Mexico, and so much more. A short drive off the Key options await you including national hotel chains and affordable beach-inspired tiny house micro-rentals.
Search
customize your search
Search Results for: Clear Search
Sponsored
Sunrise Cove Condominium - Oh the View!
Stay with us for your one-month vacation. We've got the best sunrise on the Key.
Sponsored
Siesta 4 Rent
Vacation condos and homes on beautiful Siesta Key, from studios to 5 bedrooms.
Casa Mar
Whether you're looking for a beachfront condo where you can unpack and dive right into all the fun or a …
The Cottages at Siesta Key
Welcome to The Cottages at Siesta Key, a charming resort close to the white, powdery sand of a great Gulf …
Spark by Hilton Sarasota Siesta Key Gateway
Offering a quiet, peaceful place to rest and relax. Treat yourself to the comfort and unmatched convenience of our newly …
Magnolia House
The Magnolia House is a tropical secluded oasis on Siesta Key. Each unit is a newly renovated 2 bedroom, 2 …
RVA, Resort Vacations
Vacation Memorably. Expansively. RVA has helped vacationers make lasting memories along Florida's Gulf Coast since 1989. We specialize in vacation …
A Beach Front Vacation
Relax in our immaculate and updated Siesta Key condo located directly on Turtle Beach at the Southern-most tip of the …
Casa Blanca Vacation Rentals
Casa Blanca Beach Resort includes Gulf-front apartments and private villas. Each villa and apartment are individually owned. The minimum stay …
Tropical Beach Resorts
Tropical Beach Resorts on Siesta Key is where you will experience the best a vacation has to offer; sugar-white sand …
Siesta Palms by the Beach
If you’re looking for a vacation rental on Siesta Key, consider the unique charm and big condo accommodations at Siesta …
Turtle Beach Campground
We're Sarasota County's premier beachfront campground. From sunrise to sunset, there's nothing like camping next to the Gulf of Mexico. …
El Presidente
We offer 38 spacious two and three bedroom fully furnished vacation rental condominiums right on the beautiful beach. Our friendly …
Island Reef
Welcome To Island Reef - Paradise on beautiful Siesta Key!
Stretching from Gulf to Bay on picturesque southern Siesta Key, Island …
Aloha Kai
Five-acre vacation retreat of 68 private villas located on Siesta Key's beautiful white sand beach. All units are fully equipped. …
Captiva Beach Resort
Captiva Beach Resort is a quaint, 19-room resort located near Siesta Key's south bridge and village. From studios to two …
Fisherman's Cove
1 and 2 BR condos on 800 ft of beach. Great views of the Gulf of Mexico. Wireless high-speed internet, …
Our House At The Beach
Our House at the Beach is a two bedroom/two bath condominium complex with 106 units total. Condos are fully furnished …
Peppertree Bay
Private area on the famous, ultra white quartz sand of Crescent beach. Heated pools, fishing pier, barbecue, assigned parking, lighted …
Siesta Key Luxury Rental Properties
What sets our vacation rentals in Siesta Key, FL apart from other houses to rent? From spacious, gourmet kitchens to …
FloridaRent.com
Whether you're looking for a relaxing beach cottage or a modern beach front condo look no further! We have provided …
Siesta Key Palms Resort
Fully renovated retro hotel features the ultimate in modern amenities while keeping its historical mid century integrity and charm. All …
Altez Vacations
Altez Vacations is a family owned and operated vacation rental management company on Siesta Key. As natives of Sarasota we …
Florida Rental By Owners
Discover the freedom of vacationing on your terms with Florida Rental By Owners. As the premier vacation rental listing site, …
Harbor Towers Yacht & Racquet Club
Harbor Towers is a tropical paradise on Siesta Key which has long been considered one of the gulf coast's most …
Midnight Cove
1-week minimum stay accommodations on Crescent Beach. Our luxury 2 and 3 bedroom vacation rentals are furnished with the conveniences …
Calini Beach Club
Calini Beach Club’s luxurious, 1,300 square foot, two bedroom/two bath condos await your visit. Units have fully-equipped kitchens, private verandas …
The Palm Bay Club
The Palm Bay Club is a Siesta Key Florida beachfront vacation rental resort condominium property offering three types of accommodations, …
Ascendia Group | Real Estate | Rentals | Property Management
Ascendia Group is an award-winning one-stop for real estate (buying and selling), property management (vacation homes, annual & seasonal rentals), …
White Sands Village
Seven acres with fully equipped one and two bedroom condos on tropical grounds. Facilities include a heated pool, barbeque grills, …
Siesta Leona House
A deluxe vacation rental property on the intercoastal waterway. Steps to Siesta Key Village. Features include heated pool, enclosed lanai, …
Sunset Royale
Sunset Royale offers one and two bedroom condos fully equipped with all the amenities, including a full kitchen to make …
Hyatt Residence Club Sarasota, Siesta Key Beach
An oasis of island calm just feet from the Gulf of Mexico, our spacious condo-style accommodations range from 1800 to …
House of the Sun
House of the Sun features fully furnished two-bedroom, two-bathroom units with private balconies, full kitchens, and access to all on-site …
Siesta Key Beachside Villas
Our quiet, quaint, coastal-concept retreat offers beach access. 17-units with a variety of room types. Located within walking distance to …
Sea Club V Beach Resort
Welcome to Sea Club V Beach Resort, where you'll be doing more than taking a family vacation, you'll find yourself …
Tivoli by the Sea
Welcome to Tivoli by the Sea Resort...your ultimate vacation getaway. Tivoli is a luxurious condominium on beautiful Siesta Key. As …
Crescent Arms Vacation Rentals
If you want to enjoy the sugar-white sand of Crescent Beach, shop or just relax by the pool - Crescent …
Rent Siesta Key
We offer an unrivaled selection of vacation rentals throughout Siesta Key and the Sarasota/Bradenton Gulf Coast. Discover a spectacular paradise …
Next To The Best
On beautiful Siesta Key, all our properties are within walking distance to the world's best beach and near the Village …
Siesta Key Beach Resort and Suites
We offer a location like no other, as we’re the only hotel in Siesta Key Village. Only a minutes-walk across …
The Cottages on the Key
We understand what makes a luxury vacation home right for you. We make it our business to find a vacation …
Sunrise Cove
Make your next vacation one to remember at Sunrise Cove Condominium on Siesta Key. Our monthly vacation rental condos are …
Siesta Sun Beach Villas
We are your destination if you are searching for an “Old Florida” feel with all of the modern updates! Units …
The Capri at Siesta
All of our rooms are comfortably furnished with kitchenettes, premium beds, and large flat screen TVs all with surprisingly competitive, …
Cunningham Property Management
Whether you're looking for the world famous white-sand of Crescent Beach on Siesta Key, love the serenity of Longboat Key …
Midnight Cove II
Siesta Key's Midnight Cove II has bayside condos located on 14 lush acres with access to Crescent Beach. We're just …
Home & Condo Rentals and Property Management
For your next vacation or seasonal rental on Siesta Key we offer many types of lodging including luxury waterfront condos, …
A 4 Bedroom In Siesta Key
A 4 Bedroom In Siesta Key is a beautiful four-bedroom, 3.5 bath condo with full Gulf views from the great …
Sea Shell
Sea Shell Condominium offers 49 luxurious 2BR/2BA condos, located directly on Siesta Key’s Crescent Beach. All units are fully furnished …
Island House Beach Resort
Looking for a quiet vacation spot on the best beach in America? The Island House offers a variety of apartments …
Tropical Breeze Resort
Our resort hotel has a central location with lush, tropical garden landscaping. Two heated pools, a spa, BBQ grills, tiki …
Tropical Sands Accommodations
We are the largest vacation rental management company on Siesta Key! From studios to 9 bedrooms. Most units offer free …
Lido Beach Resort
Our Sarasota luxury resort invites you to kick back and take in the picturesque views from our white sand beach, …
Siesta Key Vacation Apartments
Boutique style property less than a mile from Siesta Beach. Close to the Gulf without the congestion of larger properties. …
Siesta Breakers
Beyond the entry gate to this luxury condominium resort, you will find everything you would want for an island retreat. …
SK Sand Dollar - A Condo at Crescent Arms
A luxury condo on one of the world's Top Ten beaches. Enjoy a spectacular view of the Gulf of Mexico …
The Beach Club at Siesta Key
Located in the heart of picturesque Siesta Key, Florida sits this award-winning nightly resort. White-sand quartz beaches combined with a …
Siesta Gulf View
Siesta Gulf View is directly on world famous Siesta Beach, with its incredible sugar white crystal sands. Limited monthly Gulf …
iTrip Vacations Sarasota & Venice
iTrip Vacations offers a variety of vacation home rentals from homes to condos 5 star service
Crystal Sands
Whether you’re looking for a retreat with your loved one or planning a family vacation, Crystal Sands has something for …
FloridaRentals.com
We offer the highest quality vacation rentals in Siesta Key: romantic beachfront condos, expansive homes and everything in between. Trusted …
Sea Spray Resort
Steps away from award-winning Siesta Beach, Sea Spray Resort is the ideal place to stay while visiting the Sarasota area. …
Siesta 4-Rent
We offer Studios - 5 bedroom condos and homes on beautiful Siesta Key. All units are fully equipped, most directly …
The Inn on Siesta Key
Looking for vintage Florida with coastal flair? The Inn on Siesta Key sits across the street from Siesta Beach, the …
Excelsior Beach to Bay
Excelsior Condominiums’ luxury 2 and 3 bedroom condos are located on the beautiful, white sand beaches of world-famous Siesta Key. …
Stringer Management
Established in 1991, we are a 2nd generation family run business along with our “Team Stringer” representatives. Stringer Management has …
Gulf & Bay Club
Gulf & Bay Club offers two and three bedroom/two bath units on the beautiful award winning white sand beach of …
Beachside Management
Let us assist with your Siesta Key vacation rental. Whether condo, bungalow, studio villa or 5 bedroom home we have …
Crescent Royale
You can’t find a better condo on Siesta Key for your romantic getaway, family vacation or business event. Enjoy amazing …
Lido Key Vacations
Lido Key is a cozy island vacation getaway in Sarasota that remains a bit of a hidden gem. For travelers …
Peaks & Palms Vacation Rental
Steps to the beach, and quick access to shops and dining, this condo offers style and comfort with many updates …
Sandpiper Beach Club
The Sandpiper Beach Club offers you a beachfront home on Siesta Key, a subtropical haven with glistening white sands, graceful …
Siesta Bungalows
Be a true Siesta Key local by staying with Siesta Bungalows. Choose from six old-world-Florida bungalows surrounded by tropical gardens …
Horizons West
Located on top-rated Crescent Beach on beautiful Siesta Key. Beach to bay, 1, 2 & 3 bedroom Gulf front apartments …
Siesta Sands on the Beach
Siesta Sands on the Beach is directly on the beach. All condos are completely furnished with full kitchen, living room, …
A Castle on the Key
This enchanting 5 bedroom, 4.5 bath, two-story, canal-front ‘castle-like,’ private home with pool and spa is situated on Siesta Key …
Jamaica Royale
Create the perfect setting for the type of vacation you deserve in one of our studio, one bedroom, or two …
127 Beach Road
Open floor plan brings game room (with pool table), living room and kitchen together. Two guest bedrooms on second level. …
Hibiscus Suites
Located at the gateway of Siesta Key enjoy 43 spacious guest rooms, studios, one and two bedroom suites.
Along with the …
The Anchorage
While private beach access is included with your stay, we also have a wide variety of things to do onsite …
Ten35 Seaside
Relax and unwind at our spectacular new vacation rentals, where modern luxury meets the natural beauty of Siesta Key. We …
Siesta Dunes
Siesta Dunes is a beach condominium community located on Siesta Key, a barrier island on Florida's west coast. Two and …
Siesta Royale
A taste of ''Old Florida'' with modern amenities! Siesta Royale is a smoke-free Gulf-front property with one and two bedroom …
SkyRun Sarasota Vacation Rentals
SkyRun Vacation Rentals is the premier short-term rental property management company serving Sarasota and surrounding beaches, including Siesta Key, Lido …
All Sunnyside Properties
Sunnyside Properties is a family-owned and operated full-service property Management Company specializing in vacation rentals on Siesta Key. We have …