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.

customize your search

Search Results for: Clear Search
Tiny House Siesta
Whether it is a 1st floor bedroom you seek, a 3 bedroom model, or a pet friendly tiny, we're sure …
Beach Terrace Condominium
This high-rise building looks out over the north side of the Siesta Key barrier reef, affording residents incredibly breathtaking views …
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 …
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 …
La Siesta Condominiums
Tastefully furnished beach front vacation units with one or two bedrooms – each privately owned and maintained by their owners. …
Siesta Leona House
Introducing, a deluxe vacation property in the Village of Siesta on the intercoastal waterway. Key features include, heated pool, enclosed …
Tropical Beach Resorts
Tropical Beach Resorts on Siesta Key is where you will experience the best a vacation has to offer; sugar-white sand …
Jamaica Royale
Create the perfect setting for the type of vacation you deserve in one of our studio, one bedroom, or two …
A Condo Facing Siesta Key Beach
2BR/2BA with king beds. Across from Siesta Beach, offers view from porch, living and dining rooms, kitchen and bedroom. Heated …
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 …
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 …
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, …
Tropical Siesta Vacations
Vacation Rentals and Property Management Services
Sea Spray Resort
Steps away from award-winning Siesta Beach, the Sea Spray Resort is the ideal place to stay while visiting the Sarasota …
Siesta Key Palms Resort
Fully renovated retro hotel features the ultimate in modern amenities while keeping its historical mid century integrity and charm. All …
Rent Siesta Now
A family owned and operated collection of thirteen luxury vacation properties. Providing an exceptionally clean and fully stocked home …
Siesta Bungalows
We are a local family of three that rents out cozy and private bungalows in Palm Island neighborhood in the …
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 …
The Beach Place
Considered one of the finest Siesta Key vacation rentals, The Beach Place is a quiet oasis of cozy cottage apartments …
Siesta Key Inn
Siesta Key Inn is an intimate eight unit condominium complex that is operated with the ambiance of a family run …
Siesta Breakers Condominium
Beyond the entry gate to this luxury condominium resort, you will find everything you would want for an island retreat. …
Ringling Beach House
A private tropical paradise reminiscent of days gone by, steps from the powdery white sand and crystal-clear blue waters of …
Island House Beach Resort
Looking for a quiet vacation spot on the best beach in America? The Island House offers a variety of apartments …
FloridaRent.com
Whether you're looking for a relaxing beach cottage or a modern beach front condo look no further! We have provided …
Midnight Cove
From the Beach to the Bay, Midnight Cove offers Premium, Family-Friendly (One Week Minimum Stay) Condominium and Townhouse Accommodations in …
Gulf Haven Condominium
Monthly rental villas, one, two and three bedroom units available. Located on beautiful Crescent Beach on Siesta Key
Argus Property Management
Argus can make all your vacation dreams come true! We have more than 300 Siesta Key rental condominiums ... all …
Siesta Key Bungalows
Siesta Key Bungalows is a ''peaceful tropical paradise, located a short distance from Siesta Beach'', surrounded by ''exotic palm trees, …
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 …
El Presidente Condominium
We offer 38 spacious two and three bedroom fully furnished vacation rental condominiums, with 5 floor plans to choose from …
Sarasota Surf & Racquet Club
Sarasota Surf and Racquet Club is right around the corner from the famous Siesta Key Village, where you will find …
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 Club V Beach Resort
Sea Club V Beach Resort is situated directly on the Gulf of Mexico in beautiful Siesta Key, Florida. We have …
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, …
Island Reef Owners Association
Welcome To Island Reef - Paradise on beautiful Siesta Key! Stretching from Gulf to Bay on picturesque southern Siesta Key, Island …
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 Capri at Siesta
All of our rooms are comfortably furnished with kitchenettes, premium beds, and large flat screen TVs all with surprisingly competitive, …
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 …
iTrip Vacations Sarasota & Venice
iTrip Vacations offers affordable vacation home rentals at lower prices than competitors, saving you time and money.
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 …
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 …
Siesta Sands Beach Resort
Siesta Sands Beach Resort is the perfect vacation spot. Located directly on the #1 beach in the country, spend your …
Sandpiper Beach Club
The Sandpiper Beach Club offers you a beachfront home on Siesta Key, a subtropical haven with glistening white sands, graceful …
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 …
White Sands Village Condominium
Seven acres with fully equipped one and two bedroom condos on tropical grounds. Facilities include a heated pool, barbeque grills, …
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 …
Hyatt Residence Club Sarasota, Siesta Key Beach
Relax with gulf views and the ocean breeze on the private terrace or patio of one of the 44 resident-style …
Carrie's Rentals
There is NO other condo complex on Siesta Key that is as close to the ocean. You can practically throw …
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, …
Altez Vacations
Every vacation should be unique, dynamic and distinct. Find our homes in the sugar sands of Siesta Key, and beyond. …
Captiva Beach Resort
Captiva Beach Resort is a quaint, 19 room resort located at the South end of Siesta Key. From Studios to …
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 …
Sunset Beach Resort
Sunset Beach Resort is a destination wedding venue specializing in beach weddings in Siesta Key, Florida. The venue is a …
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 …
Siesta Sunset Royale
Our seven apartment beach house is located 100 yards from the beach at Access #7 and one-block from the tropical …
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), …
Ameniti Bay 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 …
Magnolia House
The Magnolia House is a tropical secluded oasis on Siesta Key. Each unit is a newly renovated 2 bedroom, 2 …
Holiday Inn Express & Suites Sarasota East I-75
A short drive to Siesta Key and easily accessible from I-75 exit 205 and Sarasota-Bradenton Intl Airport (SRQ). All hotel …
My Old Florida, LLC
Secluded 3 bedroom 2 bath home located on the Grand Canal with boating access to Sarasota Bay. An easy walk …
Siesta Gulf View
Siesta Gulf View is directly on world famous Siesta Beach, with its incredible sugar white crystal sands. Limited monthly Gulf …
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 …
BeachPoint Cottages
Less than 100 feet to Siesta Beach Access 3B and only a 2-3 minute walk to Siesta Village, we're the …
Crystal Sands Condominium
Whether you’re looking for a retreat with your loved one or planning a family vacation, Crystal Sands has something for …
Siesta Royale
A taste of ''Old Florida'' with modern amenities! Siesta Royale is a smoke-free Gulf-front property with one and two bedroom …
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. …
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. …
Gulf & Bay Club
Gulf & Bay Club offers two and three bedroom/two bath units on the beautiful award winning white sand beach of …
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 …
SK Sand Dollar - A Condo at Crescent Arms
A luxury condo on one of the world's Top Ten beaches.
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 …
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 …
Siesta Sun Beach Villas
We are your destination if you are searching for an “Old Florida” feel with all of the modern updates! Units …
Tropical Sands Accommodations
We are the largest vacation rental management company on Siesta Key! From studios to 9 bedrooms. Most units offer free …
Fisherman's Cove
One and two bedroom vacation rentals on 800 feet of beachfront with Blind Pass Lagoon and great views of the …
Sunset Royale
Sunset Royale offers one and two bedroom condos fully equipped with all the amenities, including a full kitchen to make …
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 …
Siesta 4-Rent
We offer Studios - 5 bedroom condos and homes on beautiful Siesta Key. All units are fully equipped, most directly …
The Palm Bay Club
The Palm Bay Club is a Siesta Key Florida beachfront vacation rental resort condominium property offering three types of accommodations, …
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 …
Banyan Tree Beach Resort
Banyan Tree is your island getaway in a relaxed atmosphere with lush tropical surroundings – steps to Siesta Beach and …
127 Beach Road
Open floor plan brings game room (with pool table), living room and kitchen together. Two guest bedrooms on second level. …
Peppertree Bay
Private area on the famous, ultra white quartz sand of Crescent beach. Heated pools, fishing pier, barbecue, assigned parking, lighted …
Parrot Beach Cottages Siesta Key
Four-suite cottage steps to Siesta Beach. Enjoy spectacular sunsets, a romantic walk on the beach or relax at the pool. …
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 …
Crescent Royale Condominiums
You can’t find a better condo on Siesta Key for your romantic getaway, family vacation or business event. Enjoy amazing …
Hibiscus Suites
Located at the gateway of Siesta Key enjoy 43 spacious guest rooms, studios, one and two bedroom suites. Along with the …
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 …
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. …
Siesta Key Vacations
At Siesta Key Vacations Rentals, we understand what makes a luxury vacation home right for you.
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 …
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 Home and Condo Rentals
Carve out a piece of paradise with your very own affordable, seaside rental property. Roomy and stylish, our properties feature …
Stringer Management
Established in 1991, we are a 2nd generation family run business along with our “Team Stringer” representatives. Stringer Management has …
Vacasa
Our Siesta Key vacation homes are listed so you can easily find exactly what you’re looking for, and know exactly …
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 …
Crescent Arms Vacation Rentals
If you want to enjoy the sugar-white sand of Crescent Beach, shop or just relax by the pool - Crescent …
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 …
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 …
Lido Beach Resort
Our Sarasota luxury resort invites you to kick back and take in the picturesque views from our white sand beach, …
Horizons West
Located on top-rated Crescent Beach on beautiful Siesta Key. Beach to bay, 1, 2 & 3 bedroom Gulf front apartments …

Oops! Your search returned no results

Oops! You've filtered out the fun

Getting Around
FAQs
Visitor Center
Our Beaches
  • Sign up
    for news and
    special events
  • This field is for validation purposes and should be left unchanged.