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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Where to Stay? At Sunnyside Properties.
From beachfront rentals on the Gulf to luxury rentals near Siesta Key Village
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Relax & Unwind at Hibiscus Suites
Enjoy spacious comfort at the gateway to Siesta Key. Hibiscus Suites offers 43 inviting guest rooms and suites with full kitchens, a tropical outdoor pool and a convenient location near beaches, dining, shopping, water sports and more.
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Where Timeless Coastal Elegance Lives
Crystal Sands is a premier beachfront retreat designed for those who value comfort, beauty, and coastal living. This exclusive property offers a rare combination of refined relaxation and direct connection to the water’s edge.
Gulf Coast Vacation Rentals
Our homes are near main attractions, such as award-winning beaches, beautiful golf courses, a lively shopping and entertainment scene and …
Siesta Sands Beach Resort
Siesta Sands Beach Resort is the perfect vacation spot. Located directly on the #1 beach in the country, spend your …
Azul Siesta Key
Welcome to Azul Siesta Key, formerly The Cottages at Siesta Key, a refreshed coastal escape steps from the island’s soft …
Beach to Bay Vacation Rentals
Beach to Bay Vacation Rentals offers a stunning collection of condos on Siesta Key, Florida, perfect for a relaxing and …
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 …
Tropical Breeze Resort
Our resort hotel has a central location with lush, tropical garden landscaping. Two heated pools, a spa, BBQ grills, tiki …
Sunset Royale
Sunset Royale offers one and two bedroom condos fully equipped with all the amenities, including a full kitchen to make …
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 …
Sunrise Cove
Make your next vacation one to remember at Sunrise Cove Condominium on Siesta Key. Our monthly vacation rental condos are …
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 …
Sarasota Surf & Racquet Club
Sarasota Surf and Racquet Club is right around the corner from the famous Siesta Key Village, where you will find …
Sea Shell Vacation Rentals
Sea Shell Condominium offers 49 luxurious 2BR/2BA condos, located directly on Siesta Key’s Crescent Beach. All units are fully furnished …
Fisherman's Cove
Fisherman's Cove - Beachfront Vacation Rentals
Welcome to Fisherman's Cove, a premier collection of Gulf-front vacation rentals on Siesta Key. Nestled …
La Siesta Condominiums
Tastefully furnished beach front vacation units with one or two bedrooms – each privately owned and maintained by their owners. …
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 …
Turtle Beach Campground
Turtle Beach Campground is Sarasota County’s premier beachfront campground on Siesta Key. You are only a moment’s stroll to Turtle …
Siesta Key Palms Resort
Fully renovated retro hotel features the ultimate in modern amenities while keeping its historical mid century integrity and charm. All …
Tropical Sands Accommodations
We are the largest vacation rental management company on Siesta Key! From studios to 9 bedrooms. Most units offer free …
Gulf Coast Vacations
Offering comfort, style and unbeatable access to Florida's stunning coastline. Properties professionally managed to ensure a seamless experience, with top-tier …
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 …
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 …
Endless Summer Property Management
Welcome to Your Siesta Key Beach Escape
Endless Summer Property Management is a family-owned business dedicated to helping guests experience the …
The Beach Club at Siesta Key #106D
Steps to Crescent Beach! Beach Club #106D: Updated spacious 2BR/2BA (sleeps 6) with gated beach access. Includes 2 chairs + …
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 …
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 …
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 …
Siesta Key Beach Resort and Suites
The only hotel in Siesta Village...a location like no other. A minutes-walk across the street, take a beach chair and …
RVA, Resort Vacations
Vacation Memorably. Expansively. RVA has helped vacationers make lasting memories along Florida's Gulf Coast since 1989. We specialize in vacation …
Sea Spray Resort
Discover the new Sea Spray Resort - thoughtfully renovated and reopened in 2025. Steps from Siesta Beach and Siesta Key …
The Palm Bay Club
The Palm Bay Club is a Siesta Key Florida beachfront vacation rental resort condominium property offering three types of accommodations, …
Siesta Dunes
Siesta Dunes is a beach condominium community located on Siesta Key, a barrier island on Florida's west coast. Two and …
Crystal Sands
Welcome to Crystal Sands
Where Timeless Coastal Elegance Lives
Crystal Sands is a premier beachfront retreat designed for those who value comfort, …
Captiva Beach Resort
A Boutique Hotel Along the Crystal Shores of Florida’s Famous Crescent Beach
Opened in 1954, Captiva Beach Resort is a charming …
Siesta 4 Rent
We offer Studios - 5 bedroom condos and homes on beautiful Siesta Key. All units are fully equipped, most directly …
Sandy Cove 1 Condo
BEAUTIFUL WHITE SANDY PRIVATE BEACH with FISHING PIER!! Your own private oasis away from the Seasonal crowds on the Public …
Pinkie Flamingo & Friends
With 20+ years of marketing and management experience, exceptional attention to detail, and a love for the boutique experience, we …
Siesta Key Home Rental
Experience luxury beachfront living with Siesta Key Home Rental. Choose from 3 unique properties, steps from the sand, offering relaxation, …
Siesta Key Island Rentals
Siesta Key Island Rentals is a collection of professionally managed properties and units. Our vacation rentals are convenient to restaurants …
iTrip Vacations Sarasota & Venice
iTrip Vacations offers a variety of vacation home rentals from homes to condos 5-star service
El Presidente
We offer 39 spacious two and three bedroom fully furnished vacation rental condominiums right on the beautiful beach. Our friendly …
FloridaRentals.com
Discover exceptional vacation rentals in Siesta Key with FloridaRentals.com. From cozy condos to expansive homes, trusted by Florida’s top property …
Sandpiper Beach Club
The Sandpiper Beach Club offers you a beachfront home on Siesta Key, a subtropical haven with glistening white sands, graceful …
Beachside Management
Beachside Management opened in 2015 with the goal of providing wonderful vacation experiences to Siesta Key travelers. We offer a …
Home & Condo Rentals and Realty
For your next vacation or seasonal rental on Siesta Key we offer many types of lodging including luxury waterfront condos, …
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 …
Horizons West
Located on top-rated Crescent Beach on beautiful Siesta Key. Beach to bay, 1, 2 & 3 bedroom Gulf front apartments …
Island Reef
Welcome To Island Reef - Paradise on beautiful Siesta Key!
Stretching from Gulf to Bay on picturesque southern Siesta Key, Island …
A 4 Bedroom In Siesta Key
4BD, 3.5BA condo with Gulf view. Greatroom features 2 sofas, tv, large dining table. Sleeps 10. Located at Crescent Royale …
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 …
Gulf & Bay Club
Gulf & Bay Club offers two and three bedroom/two bath units on the beautiful award winning white sand beach of …
Gertrude Rentals
Find your perfect Siesta Key getaway with Gertrude Rentals!
Choose from 80+ professionally managed vacation rentals in Siesta Key's most desirable …
White Sands Village
Seven acres with fully equipped one and two bedroom condos on tropical grounds. Facilities include a heated pool, barbeque grills, …
Casa Mar
Whether you're looking for a beachfront condo where you can unpack and dive right into all the fun or a …
The Anchorage
While private beach access is included with your stay, we also have a wide variety of things to do onsite …
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 …
Lido Beach Resort
Our Sarasota luxury resort invites you to kick back and take in the picturesque views from our white sand beach, …
Lido Key Vacations
Lido Key is a cozy island vacation getaway in Sarasota that remains a bit of a hidden gem. For travelers …
SkyRun Vacation Rentals
SkyRun Vacation Rentals is the premier short-term rental property management company serving Sarasota and surrounding beaches, including Siesta Key, Lido …
Tropical Beach Resorts
Tropical Beach Resorts on Siesta Key is where you will experience the best a vacation has to offer; sugar-white sand …
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 …
Magnolia House
The Magnolia House is a tropical secluded oasis on Siesta Key. Each unit is a newly renovated 2 bedroom, 2 …
Sea Crest
Welcome to Sea Crest on Siesta Key. If you are looking for a friendly beachfront environment, then Sea Crest is …
Altez Vacations
Altez Vacations is a family owned and operated vacation rental management company on Siesta Key. As natives of Sarasota we …
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 …
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 Bungalows
6 old-world-Florida bungalows surrounded by tropical gardens to spend a month or more immersing yourself in the Siesta Key lifestyle. …
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 Breakers
Beyond the entry gate to this luxury condominium resort, you will find everything you would want for an island retreat. …
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), …
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 …
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, …
Roelens Vacations
Offering a variety of rentals to suit different preferences and needs. Selections include charming single-family homes, luxurious waterfront properties, and …
Siesta Gulf View
Siesta Gulf View is directly on world famous Siesta Beach, with its incredible sugar white crystal sands. Limited monthly Gulf …
Siesta Sun Beach Villas
We are your destination if you are searching for an “Old Florida” feel with all of the modern updates! Units …
Crescent Royale
Welcome to Crescent Royale Condominiums featuring family friendly, relaxing, and comprehensive Siesta Key condo rentals. If you are looking for …
Turtle Beach Resort
Discover Siesta Key’s premier hidden gem: an Old Florida waterfront retreat with private cottages, bay views, and kayaking to Midnight …
Jamaica Royale
Create the perfect setting for the type of vacation you deserve in one of our studio, one bedroom, or two …
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 …
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. …
Island House Beach Resort
Looking for a quiet vacation spot on the best beach in America? The Island House offers a variety of apartments …
Siesta Key Inn
Welcome to Siesta Key Inn, your ideal Siesta Key vacation rental for a memorable getaway. Nestled just a short 5-minute …