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 Cottages at Siesta Key Await
Find this charming resort close to the white, powdery sand of Crescent Beach.
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Tropical Sands Accommodations
All our Vacation Rentals are located on world-famous Siesta Key.
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The Palm Bay Club for Your Next Vacation
With a 3-night minimum stay, we're the ideal choice for your Siesta Key vacation
Magnolia House
The Magnolia House is a tropical secluded oasis on Siesta Key. Each unit is a newly renovated 2 bedroom, 2 …
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 …
Gulf & Bay Club
Gulf & Bay Club offers two and three bedroom/two bath units on the beautiful award winning white sand beach of …
Stringer Management
Established in 1991, we are a 2nd generation family run business along with our “Team Stringer” representatives. Stringer Management has …
Coastal Soul Vacations
2BR/2BA condo overlooking the yacht basin in Siesta Harbor. It includes boat dock, covered parking and deeded beach access to …
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 …
127 Beach Road
Open floor plan brings game room (with pool table), living room and kitchen together. Two guest bedrooms on second level. …
Island Reef Owners Association
Welcome To Island Reef - Paradise on beautiful Siesta Key!
Stretching from Gulf to Bay on picturesque southern Siesta Key, Island …
FloridaRentals.com
We offer the highest quality vacation rentals in Siesta Key: romantic beachfront condos, expansive homes and everything in between. Trusted …
Tropical Breeze Resort
Our resort hotel has a central location with lush, tropical garden landscaping. Two heated pools, a spa, BBQ grills, tiki …
Captiva Beach Resort
Captiva Beach Resort is a quaint, 19 room resort located at the South end of Siesta Key. From Studios to …
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 …
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 …
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 …
SkyRun Sarasota
SkyRun Vacation Rentals is the premier short-term rental property management company serving Sarasota and surrounding beaches, including Siesta Key, Lido …
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 4-Rent
We offer Studios - 5 bedroom condos and homes on beautiful Siesta Key. All units are fully equipped, most directly …
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 …
469 Canal Road
This luxurious fully updated and remodeled 4 bedroom 3 bath townhome is in the heart of Siesta Key. Perfect to …
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 …
Sea Spray Resort
Steps away from award-winning Siesta Beach, the Sea Spray Resort is the ideal place to stay while visiting the Sarasota …
Island House Beach Resort
Looking for a quiet vacation spot on the best beach in America? The Island House offers a variety of apartments …
El Presidente Condominium
We offer 38 spacious two and three bedroom fully furnished vacation rental condominiums right on the beautiful beach. Our friendly …
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 …
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 …
FloridaRent.com
Whether you're looking for a relaxing beach cottage or a modern beach front condo look no further! We have provided …
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 …
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 …
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 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 …
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 …
Beachside Management, LLC
Let us assist with your Siesta Key vacation rental. Whether you prefer a condo, bungalow, studio villa, or 5 bedroom …
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 …
Vacasa
Our Siesta Key vacation homes are listed so you can easily find exactly what you’re looking for, and know exactly …
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 …
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), …
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 …
Siesta Leona House
Introducing, a deluxe vacation property in the Village of Siesta on the intercoastal waterway. Key features include, heated pool, enclosed …
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 …
Crescent Royale Condominiums
You can’t find a better condo on Siesta Key for your romantic getaway, family vacation or business event. Enjoy amazing …
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 …
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 …
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 …
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 …
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 …
The Palm Bay Club
The Palm Bay Club is a Siesta Key Florida beachfront vacation rental resort condominium property offering three types of accommodations, …
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 …
Sarasota Surf & Racquet Club
Sarasota Surf and Racquet Club is right around the corner from the famous Siesta Key Village, where you will find …
Sunset Royale
Sunset Royale offers one and two bedroom condos fully equipped with all the amenities, including a full kitchen to make …
Crystal Sands Condominium
Whether you’re looking for a retreat with your loved one or planning a family vacation, Crystal Sands has something for …
Tropical Sands Accommodations
We are the largest vacation rental management company on Siesta Key! From studios to 9 bedrooms. Most units offer free …
Peppertree Bay
Private area on the famous, ultra white quartz sand of Crescent beach. Heated pools, fishing pier, barbecue, assigned parking, lighted …
Argus Vacation Rentals
Whether you want a quiet spot to enjoy the tropical weather or a vacation spot to drop into between fun …
Fisherman's Cove
1 and 2 BR condos on 800 ft of beach. Great views of the Gulf of Mexico. Wireless high-speed internet, …
Siesta Bungalows
We are a local family of three that rents out cozy and private bungalows in Palm Island neighborhood in 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. …
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 …
Hibiscus Suites
Located at the gateway of Siesta Key enjoy 43 spacious guest rooms, studios, one and two bedroom suites.
Along with the …
Beach Terrace Condominium
A short stroll to the beach and village, Beach Terrace Condominium overlooks the Gulf of Mexico and the north end …
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 …
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 …
Midnight Cove
1-week minimum stay accommodations on Crescent Beach. Our luxury 2 and 3 bedroom vacation rentals are furnished with the conveniences …
The Capri at Siesta
All of our rooms are comfortably furnished with kitchenettes, premium beds, and large flat screen TVs all with surprisingly competitive, …
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. …
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 …
Anchorage Yacht & Tennis Club
While private beach access is included with your stay, we also have a wide variety of things to do onsite …
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, …
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 Palms Resort
Fully renovated retro hotel features the ultimate in modern amenities while keeping its historical mid century integrity and charm. All …
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 …
Siesta Sands Beach Resort
Siesta Sands Beach Resort is the perfect vacation spot. Located directly on the #1 beach in the country, spend your …
White Sands Village Condominium
Seven acres with fully equipped one and two bedroom condos on tropical grounds. Facilities include a heated pool, barbeque grills, …
Crescent Arms Vacation Rentals
If you want to enjoy the sugar-white sand of Crescent Beach, shop or just relax by the pool - Crescent …
Siesta Sun Beach Villas
We are your destination if you are searching for an “Old Florida” feel with all of the modern updates! Units …
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 …
Horizons West
Located on top-rated Crescent Beach on beautiful Siesta Key. Beach to bay, 1, 2 & 3 bedroom Gulf front apartments …
Siesta Breakers Condominium
Beyond the entry gate to this luxury condominium resort, you will find everything you would want for an island retreat. …
Sandpiper Beach Club
The Sandpiper Beach Club offers you a beachfront home on Siesta Key, a subtropical haven with glistening white sands, graceful …
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 …
Altez Vacations
Every vacation should be unique, dynamic, and distinctive. Find our homes on the sugar sands of Siesta Key, and beyond. …
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, …
Siesta Gulf View
Siesta Gulf View is directly on world famous Siesta Beach, with its incredible sugar white crystal sands. Limited monthly Gulf …