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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Sarasota Surf & Racquet Club
Sarasota Surf and Racquet Club is right around the corner from the famous Siesta Key Village, where you will find …
RVA, Resort Vacations
Vacation Memorably. Expansively. RVA has helped vacationers make lasting memories along Florida's Gulf Coast since 1989. We specialize in vacation …
Vacasa
Our Siesta Key vacation homes are listed so you can easily find exactly what you’re looking for, and know exactly …
Island Reef Owners Association
Welcome To Island Reef - Paradise on beautiful Siesta Key! Stretching from Gulf to Bay on picturesque southern Siesta Key, Island …
SK Sand Dollar - A Condo at Crescent Arms
A luxury condo on one of the world's Top Ten beaches.
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 …
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 …
SkyRun Sarasota
SkyRun Vacation Rentals is the premier short-term rental property management company serving Sarasota and surrounding beaches, including Siesta Key, Lido …
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 …
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 Bayside Vacation Rentals
Our spacious units, individually owned and decorated, are surrounded by lush, tropical landscaping, shell paths, and quiet lakes with soothing …
Siesta Sands Beach Resort
Siesta Sands Beach Resort is the perfect vacation spot. Located directly on the #1 beach in the country, spend your …
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 Bungalows
We are a local family of three that rents out cozy and private bungalows in Palm Island neighborhood in 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 …
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 …
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, …
Siesta Key Palms Resort
Fully renovated retro hotel features the ultimate in modern amenities while keeping its historical mid century integrity and charm. All …
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. …
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 Spray Resort
Steps away from award-winning Siesta Beach, the Sea Spray Resort is the ideal place to stay while visiting the Sarasota …
Rent Siesta Key
We offer an unrivaled selection of vacation rentals throughout Siesta Key and the Sarasota/Bradenton Gulf Coast. Discover a spectacular paradise …
Fisherman's Cove
One and two bedroom vacation rentals on 800 feet of beachfront with Blind Pass Lagoon and great views of the …
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 …
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 …
Argus Vacation Rentals
Whether you want a quiet spot to enjoy the tropical weather or a vacation spot to drop into between fun …
Crescent Royale Condominiums
You can’t find a better condo on Siesta Key for your romantic getaway, family vacation or business event. Enjoy amazing …
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 …
The Capri at Siesta
All of our rooms are comfortably furnished with kitchenettes, premium beds, and large flat screen TVs all with surprisingly competitive, …
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 …
El Presidente Condominium
We offer 38 spacious two and three bedroom fully furnished vacation rental condominiums, with 5 floor plans to choose from …
The Palm Bay Club
The Palm Bay Club is a Siesta Key Florida beachfront vacation rental resort condominium property offering three types of accommodations, …
Beach Terrace Condominium
A short stroll to the beach and village, Beach Terrace Condominium overlooks the Gulf of Mexico and the north end …
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 …
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 …
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 …
Horizons West
Located on top-rated Crescent Beach on beautiful Siesta Key. Beach to bay, 1, 2 & 3 bedroom Gulf front apartments …
BeachPoint Cottages
Less than 100' to Siesta Beach Access 3B & only a 2-3 minute walk to Siesta Village. The most walkable …
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), …
Tropical Breeze Resort
Two heated pools, spa, BBQ grill and tiki huts in lush landscape. Complimentary beach chairs, towels and bikes make playing …
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, …
Beachside Management, LLC
Let us assist with your Siesta Key vacation rental. Whether you prefer a condo, bungalow, studio villa, or 5 bedroom …
Altez Vacations
Every vacation should be unique, dynamic, and distinctive. Find our homes on the sugar sands of Siesta Key, and beyond. …
Anchorage Yacht & Tennis Club
While private beach access is included with your stay, we also have a wide variety of things to do onsite …
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 …
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 …
Siesta Royale
A taste of ''Old Florida'' with modern amenities! Siesta Royale is a smoke-free Gulf-front property with one and two bedroom …
Siesta Breakers Condominium
Beyond the entry gate to this luxury condominium resort, you will find everything you would want for an island retreat. …
Tropical Sands Accommodations
We are the largest vacation rental management company on Siesta Key! From studios to 9 bedrooms. Most units offer free …
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 …
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 …
Best Western Plus Siesta Key Gateway
Offering a quiet, peaceful place to rest and relax. Treat yourself to the comfort and unmatched convenience of our newly …
Ameniti Bay Sarasota Hotel & Suites
Behind every great day is a great night - a stay with us ensures you're at your best, whether travelling …
Magnolia House
The Magnolia House is a tropical secluded oasis on Siesta Key. Each unit is a newly renovated 2 bedroom, 2 …
Siesta Gulf View
Siesta Gulf View is directly on world famous Siesta Beach, with its incredible sugar white crystal sands. Limited monthly Gulf …
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 …
Peppertree Bay
Private area on the famous, ultra white quartz sand of Crescent beach. Heated pools, fishing pier, barbecue, assigned parking, lighted …
Siesta Sun Beach Villas
We are your destination if you are searching for an “Old Florida” feel with all of the modern updates! Units …
Siesta 4-Rent
We offer Studios - 5 bedroom condos and homes on beautiful Siesta Key. All units are fully equipped, most directly …
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 …
FloridaRentals.com
We offer the highest quality vacation rentals in Siesta Key: romantic beachfront condos, expansive homes and everything in between. Trusted …
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 …
Jamaica Royale
Create the perfect setting for the type of vacation you deserve in one of our studio, one bedroom, or two …
Tiny House Siesta
Whether it is a 1st floor bedroom you seek, a 3 bedroom model, or a pet friendly tiny, we're sure …
Coastal Soul Vacations
2BR/2BA condo overlooking the yacht basin in Siesta Harbor. It includes boat dock, covered parking and deeded beach access to …
FloridaRent.com
Whether you're looking for a relaxing beach cottage or a modern beach front condo look no further! We have provided …
Peaks & Palms Vacation Rental Group
Steps to the beach, and quick access to shops and dining, this condo offers style and comfort with many updates …
Hibiscus Suites
Located at the gateway of Siesta Key enjoy 43 spacious guest rooms, studios, one and two bedroom suites. Along with the …
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. …
iTrip Vacations Sarasota & Venice
iTrip Vacations offers affordable vacation home rentals at lower prices than competitors, saving you time and money.
Crescent Arms Vacation Rentals
If you want to enjoy the sugar-white sand of Crescent Beach, shop or just relax by the pool - Crescent …
Tropical Beach Resorts
Tropical Beach Resorts on Siesta Key is where you will experience the best a vacation has to offer; sugar-white sand …
White Sands Village Condominium
Seven acres with fully equipped one and two bedroom condos on tropical grounds. Facilities include a heated pool, barbeque grills, …
Siesta Leona House
Introducing, a deluxe vacation property in the Village of Siesta on the intercoastal waterway. Key features include, heated pool, enclosed …
Stringer Management
Established in 1991, we are a 2nd generation family run business along with our “Team Stringer” representatives. Stringer Management has …
Midnight Cove
From the Beach to the Bay, Midnight Cove offers Premium, Family-Friendly (One Week Minimum Stay) Condominium and Townhouse Accommodations in …
Sunset Royale
Sunset Royale offers one and two bedroom condos fully equipped with all the amenities, including a full kitchen to make …
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 …
The Beach Place
Considered one of the finest Siesta Key vacation rentals, The Beach Place is a quiet oasis of cozy cottage apartments …
Sandpiper Beach Club
The Sandpiper Beach Club offers you a beachfront home on Siesta Key, a subtropical haven with glistening white sands, graceful …
469 Canal Road
This luxurious fully updated and remodeled 4 bedroom 3 bath townhome is in the heart of Siesta Key. Perfect to …
127 Beach Road
Open floor plan brings game room (with pool table), living room and kitchen together. Two guest bedrooms on second level. …
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 …
Banyan Tree Beach Resort
We offer cozy Siesta Key accommodations just a short walk away from award-winning Siesta Beach. Clustered together in a pleasant …
Lido Beach Resort
Our Sarasota luxury resort invites you to kick back and take in the picturesque views from our white sand beach, …
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 …
Captiva Beach Resort
Captiva Beach Resort is a quaint, 19 room resort located at the South end of Siesta Key. From Studios to …
Island House Beach Resort
Looking for a quiet vacation spot on the best beach in America? The Island House offers a variety of apartments …
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 …
Gulf & Bay Club
Gulf & Bay Club offers two and three bedroom/two bath units on the beautiful award winning white sand beach of …
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 …

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