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.

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The Anchorage on Siesta Key
While private beach access is included with your stay, we also have a wide variety of things to do onsite …
Tropical Siesta Vacations
Vacation Rentals and Property Management Services
Tiny House Siesta
Each Tiny House Siesta has it's own unique features that set it apart.
A 4 Bedroom In Siesta Key
A 4 Bedroom In Siesta Key is a beautiful 4 bedroom, 3.5 bath condo with full Gulf views from the …
Secrest Island Home in Paradise
Newly remodeled, single family home, 3 bedrooms, 2 baths, enclosed screened-in 27 x 13 heated outside pool(set to 82 degrees) …
Beach Terrace Condominium
This high-rise building looks out over the north side of the Siesta Key barrier reef, affording residents here incredibly breathtaking …
La Siesta Condo Association
We are the closest condominium complex to Siesta Beach – ranked the #1 Beach in the USA by Tripadvisor, the …
Beach Place
Considered one of the finest Siesta Key vacation rentals, The Beach Place is a quiet oasis of cozy cottage apartments …
Ascendia Group | Real Estate | Property Management | Insurance
Ascendia Group is an award-winning one-stop for real estate (buying and selling), property management (vacation homes, annual & seasonal rentals), …
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 …
My Old Florida LLC
Secluded 3 bedroom 2 bath home located on the Grand Canal with boating access to Sarasota Bay. An easy walk …
Fisherman's Cove
One and two bedroom vacation rentals on 800 feet of beachfront with Blind Pass Lagoon and great views of the …
Ameniti Bay and Magnolia Pointe, Sarasota Hotel & Suites
Two boutique-style hotels at one location with complimentary breakfast, Jacuzzi suites, microwaves, refrigerators, resort style, zero-entry pool, sundeck, fire pits …
Crystal Sands Condominium
Whether you’re looking for a retreat with your loved one or planning a family beach vacation, Crystal Sands on Siesta …
Siesta Royale
A taste of ''Old Florida'' with modern amenities! Siesta Royale is a smoke-free Gulf-front property with one and two bedroom …
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 Inn
Siesta Key Inn is an intimate eight unit condominium complex which is operated with the ambiance of a family run …
Siesta Key Bungalows
Siesta Key Bungalows is a ''peaceful tropical paradise, located a short distance from Siesta Key Beach'', surrounded in ''exotic palm …
Gulf & Bay Club
Gulf & Bay Club offers two and three bedroom/two bath units on the beautiful award winning white sand beach of …
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 Bungalows
We are a local family of three (Ali and Rich Light with our daughter Chloe! ???????? ) that rent …
Sea Spray Resort
Steps away from award-winning Siesta Key Beach, the Sea Spray Resort is the ideal place to stay while visiting the …
Jennette Properties
Welcome to Jennette Properties, the premier site to discover the most desirable, luxury seasonal vacation properties, along with luxury long-term …
Ringling Beach House
Our units range in size from adorable efficiencies to fresh and fun 2 bedroom units to spacious 3 bedroom units.
Sarasota Surf & Racquet Club
Sarasota Surf and Racquet Club is right around the corner from the famous Siesta Key Village, where you will find …
iTrip Vacations Sarasota & Venice
iTrip Vacations offers affordable vacation home rentals at lower prices than competitors, saving you time and money.
Banyan Tree Beach Resort
Banyan Tree is your island getaway in a relaxed atmosphere with lush tropical surroundings – steps to Siesta Beach and …
House of the Sun Condominiums
House of the Sun features fully furnished two-bedroom, two-bathroom units with private balconies, full kitchens, and access to all on-site …
Mermaid Villas
2BR, 2½ BA. Washer & dryer in laundry room. Covered parking, microwave, VCR/TV, beach access across the street. Bikes, access …
Siesta Key Palms Resort
This fully renovated retro hotel features the ultimate in modern amenities while keeping its historical mid century integrity and charm. …
The Palm Bay Club
The Palm Bay Club is a Siesta Key Florida beachfront vacation rental resort condominium property offering three types of accommodations, …
Crescent Arms Vacation Rentals
If you want to enjoy the sugar-white sand of Crescent Beach, shop or just relax by the pool - Crescent …
Crescent Royale Condominiums
Welcome to Crescent Royale Condominiums featuring family friendly, relaxing and comprehensive Siesta Key condo rentals. If you are looking for …
Gulf Haven Condominium
Monthly rental villas, one, two and three bedroom units available. Located on beautiful Crescent Beach, Siesta Key, Florida
Siesta Palms by the Beach
Let the sweet smell of Plumeria greet you as you step into the charming paradise of their unique island accommodations. …
Hibiscus Suites
Located at the gateway of Siesta Key enjoy 43 spacious guest rooms, studios, one and two bedroom suites. Along with the …
Siesta Gulf View
Siesta Gulf View is directly on world famous Siesta Key Beach, with its incredible sugar white Crystal Sands. Limited Monthly Gulf …
Sunrise Cove Condominium
What makes Sunrise Cove, your Siesta Key beach destination, so unforgettable? We've heard it's because our resort is the most …
A Condo Facing Siesta Key Beach
2b 2b first floor directly across from Siesta Beach. Elegant Key West decor.
All Sunnyside Properties
Sunnyside Properties is a family-owned and operated full service property Management Company specializing in vacation rentals on Siesta Key. We …
Aloha Kai Vacation Rentals
Five-acre vacation retreat of 68 private villas located on Siesta Key's beautiful white sand beach. All units are fully equipped. …
Argus Property Management
Argus can make all your vacation dreams come true! We have more than 300 Siesta Key rental condominiums ... all …
FloridaRent.com
Whether you're looking for a relaxing beach cottage or a modern beach front condo look no further! We have provided …
Stringer Management
Established in 1991, we are a 2nd generation family run business along with our “Team Stringer” representatives. Stringer Management has …
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. …
A Castle on the Key
This enchanting, two-story, canal-front ‘castle-like,’ private home with pool and spa is situated on Siesta Key within a block of …
Siesta Sunset Royale
Our seven apartment beach house is located 100 yards from the beach at Access #7 and one-block from the tropical …
El Presidente Condominium
We offer 38 spacious two and three bedroom fully furnished vacation rental condominiums, with 5 floor plans to choose from …
Sandbox On The Beach
Location, location, location! All units are beachfront with breathtaking sunsets from your front deck. Our family-owned, family-friendly accommodations are directly …
Jamaica Royale
Create the perfect setting for the type of vacation you deserve in one of our studio, one bedroom, or two …
Siesta Sun Beach Villas
f you are searching for an “Old Florida” feel with all of the modern updates, Siesta Sun Beach Villas is …
Horizons West
Located on top-rated Crescent Beach on beautiful Siesta Key. Beach to bay, 1, 2 & 3 bedroom Gulf front apartments …
Siesta Sands Beach Resort
Siesta Sands Beach Resort is the perfect vacation spot. Located directly on the #1 beach in the country, spend your …
127 Beach Road
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 …
RVA, Resort Vacations
Vacation Memorably. Expansively. RVA has helped vacationers make lasting memories along Florida's Gulf Coast since 1989. We specialize in vacation …
Siesta Breakers Condominium
Beyond the entry gate to this luxury condominium resort, you will find everything you would want for an island retreat.Two …
Lido Beach Resort
Our 222 spacious guest rooms and condo-style suites, each designed to offer an island-inspired retreat, complete with Florida-inspired décor, flat …
Home & Condo Rentals and Property Management
We offer many types of lodging including luxury waterfront condos, beach resort accommodations, private homes, villas and more.
Crescent Towers Beachfront
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 …
Sunset Royale
Sunset Royale offers one and two bedroom condos fully equipped with all the amenities, including a full kitchen to make …
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 …
Peppertree Bay
Private area on the famous, ultra white quartz sand of Crescent beach. Heated pools, fishing pier, barbecue, assigned parking, lighted …
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 …
SK Sand Dollar - A Condo at Crescent Arms
A luxury condo on one of the world's Top Ten beaches.
BeachPoint Cottages
Less than 100 feet to Siesta Beach Access 3B 2-3 minute walk to Siesta Village Tropical cottages from studio size to free …
Siesta Dunes Beach Condominiums
Siesta Dunes is a beach condominium community located on Siesta Key, a barrier island on Florida's west coast. Two and …
The Capri at Siesta
All of our rooms are comfortably furnished with kitchenettes, premium beds, and large flat screen TVs all with surprisingly competitive, …
Sea Shell Condominium
Sea Shell Condominium offers 49 luxurious 2BR/2BA condos, located directly on Siesta Key’s Crescent Beach. All units are fully furnished …
Sea Club V Beach Resort
Sea Club V Beach Resort offers 6 (six) studio units, 19 (nineteen) one bedroom one bath units, 10 (ten) one …
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, …
Magnolia House
The Magnolia House is a tropical secluded oasis on Siesta Key. Each unit is a newly renovated 2 bedroom, 2 …
Siesta Leona House
Introducing, a deluxe vacation property in the Village of Siesta on the intercoastal waterway. Key features include, heated pool, enclosed …
Calini Beach Club
Luxurious 1,300 sq ft condos await your visit. Our 2BR/2BA condos offer fully equipped kitchens, private verandas, WIFI, pool & …
Midnight Cove
From the Beach to the Bay, Midnight Cove offers Premium, Family-Friendly (OneWeek Minimum Stay) Condominium and Townhouse Accommodations in the …
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 …
Island Reef Owners Association
Welcome To Island Reef - Paradise on beautiful Siesta Key! Stretching from Gulf to Bay on picturesque southern Siesta Key, Island …
Tropical Sands Accommodations
We are the largest vacation rental management company on Siesta Key! From studios to 9 bedrooms. Most units offer free …
Island House Beach Resort
Looking for a quiet vacation spot on the best beach in America? The Island House offers a variety of apartments …
Hibiscus Hideaway
Tucked between Turtle and Crescent Beaches this one-story, 3 BR/2 BA waterfront home offers a screened pool. Dining and shopping …
The Cottages on the Key
Here at The Cottages on the Key, we understand what makes a luxury vacation home right for you. We make …
White Sands Village Condominium
Seven acres with fully equipped one and two bedroom condos on tropical grounds. Facilities include a heated pool, barbeque grills, …
Sarasota Timeshare Resales & Rentals
Find an affordable timeshare resale or rental on Siesta Key within resorts like the Calini Beach Club. Timeshares are the …
Cunningham Property Management
Whether you're looking for the the world famous white-sand of Crescent Beach on Siesta Key, love the serenity of Longboat …
Sandpiper Beach Club
The Sandpiper Beach Club offers you a beachfront home on Siesta Key, a subtropical haven with glistening white sands, graceful …
Sunset Beach Resort
Sunset Beach Resort is a destination wedding venue specializing in beach weddings in Siesta Key, Florida. The venue is a …
Siesta Key Vacations
At Siesta Key Vacatons Rentals we understand what makes a luxury vacation home right for you.
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 …
Siesta Home and Condo Rentals
Carve out a piece of paradise with your very own affordable, seaside rental property. Roomy and stylish, our properties feature …
Hyatt Residence Club Sarasota, Siesta Key Beach
Hyatt Residence Club Sarasota, Siesta Key Beach is an oasis of island calm just feet away from the crystal clear …
Captiva Beach Resort
Captiva Beach Resort is a quaint, 19 room resort located at the South end of Siesta Key. From Studios to …
Beach Palms of Siesta Key Village
Enchanting Tropical Island Cottages and Beach View Suite on beautiful white Siesta Key Beach Florida with secluded patios with grills, …
Siesta 4-Rent
We offer Studios - 5 bedroom condos and homes on beautiful Siesta Key. All units are fully equipped, most directly …
Rent Siesta Now
A family owned and operated collection of thirteen luxury vacation properties. Providing an exceptionally clean and fully stocked home …
Gulf & Bay Club Bayside Vacation Rentals
Our spacious units, individually owned and decorated, are surrounded by lush, tropical landscaping, shell paths, and quiet lakes with soothing …
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 …
Best Western Plus Siesta Key Gateway
The Best Western Plus Siesta Key hotel offers a quiet, peaceful place to rest and relax. Treat yourself to the …
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 …
A Home Away From Home
This charming tropical 1,320 sq.ft. 2 bedroom 2 bath home is located within the heart of Siesta Key Village and …
Carrie's Rentals
There is NO other condo complex on Siesta Key that is as close to the ocean. You can throw a …
Altez Vacations
Every vacation should be unique, dynamic and distinct. Find our homes in the sugar sands of Siesta Key, and beyond. …

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