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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Sunrise Cove Condominium - Oh the View!
Stay with us for your one-month vacation. We've got the best sunrise on the Key.
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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.
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
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 …
Sarasota Surf & Racquet Club
Sarasota Surf and Racquet Club is right around the corner from the famous Siesta Key Village, where you will find …
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 …
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
Our resort hotel has a central location with lush, tropical garden landscaping. Two heated pools, a spa, BBQ grills, tiki …
Aloha Kai
Five-acre vacation retreat of 68 private villas located on Siesta Key's beautiful white sand beach. All units are fully equipped. …
Altez Vacations
Altez Vacations is a family owned and operated vacation rental management company on Siesta Key. As natives of Sarasota we …
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 Breakers
Beyond the entry gate to this luxury condominium resort, you will find everything you would want for an island retreat. …
Hibiscus Suites
Located at the gateway of Siesta Key enjoy 43 spacious guest rooms, studios, one and two bedroom suites.
Along with the …
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 Royale
A taste of ''Old Florida'' with modern amenities! Siesta Royale is a smoke-free Gulf-front property with one and two bedroom …
Lido Key Vacations
Lido Key is a cozy island vacation getaway in Sarasota that remains a bit of a hidden gem. For travelers …
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 …
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 …
Sandpiper Beach Club
The Sandpiper Beach Club offers you a beachfront home on Siesta Key, a subtropical haven with glistening white sands, graceful …
Turtle Beach Resort
Discover Siesta Key’s premier hidden gem: an Old Florida waterfront retreat with private cottages, bay views, and kayaking to Midnight …
Crescent Royale
Welcome to Crescent Royale Condominiums featuring family friendly, relaxing, and comprehensive Siesta Key condo rentals. If you are looking for …
Siesta Dunes
Siesta Dunes is a beach condominium community located on Siesta Key, a barrier island on Florida's west coast. Two and …
Gulf & Bay Club
Gulf & Bay Club offers two and three bedroom/two bath units on the beautiful award winning white sand beach 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 …
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 …
Siesta Sands Beach Resort
Siesta Sands Beach Resort is the perfect vacation spot. Located directly on the #1 beach in the country, spend your …
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, …
Pinkie Flamingo & Friends
With 20+ years of marketing and management experience, exceptional attention to detail, and a love for the boutique experience, we …
Siesta Bungalows
6 old-world-Florida bungalows surrounded by tropical gardens to spend a month or more immersing yourself in the Siesta Key lifestyle. …
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 …
Sea Crest
Welcome to Sea Crest on Siesta Key. If you are looking for a friendly beachfront environment, then Sea Crest is …
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 …
La Siesta Condominiums
Tastefully furnished beach front vacation units with one or two bedrooms – each privately owned and maintained by their owners. …
Casa Mar
Whether you're looking for a beachfront condo where you can unpack and dive right into all the fun or a …
Lido Beach Resort
Our Sarasota luxury resort invites you to kick back and take in the picturesque views from our white sand beach, …
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 Key Palms Resort
Fully renovated retro hotel features the ultimate in modern amenities while keeping its historical mid century integrity and charm. All …
Magnolia House
The Magnolia House is a tropical secluded oasis on Siesta Key. Each unit is a newly renovated 2 bedroom, 2 …
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 …
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 …
Roelens Vacations
Offering a variety of rentals to suit different preferences and needs. Selections include charming single-family homes, luxurious waterfront properties, and …
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 + …
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 …
The Palm Bay Club
The Palm Bay Club is a Siesta Key Florida beachfront vacation rental resort condominium property offering three types of accommodations, …
FloridaRentals.com
Discover exceptional vacation rentals in Siesta Key with FloridaRentals.com. From cozy condos to expansive homes, trusted by Florida’s top property …
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 …
Horizons West
Located on top-rated Crescent Beach on beautiful Siesta Key. Beach to bay, 1, 2 & 3 bedroom Gulf front apartments …
Beachside Management
Beachside Management opened in 2015 with the goal of providing wonderful vacation experiences to Siesta Key travelers. We offer a …
Sunrise Cove
Make your next vacation one to remember at Sunrise Cove Condominium on Siesta Key. Our monthly vacation rental condos are …
SkyRun Vacation Rentals
SkyRun Vacation Rentals is the premier short-term rental property management company serving Sarasota and surrounding beaches, including Siesta Key, Lido …
Crystal Sands
Welcome to Crystal Sands
Where Timeless Coastal Elegance Lives
Crystal Sands is a premier beachfront retreat designed for those who value comfort, …
Island Reef
Welcome To Island Reef - Paradise on beautiful Siesta Key!
Stretching from Gulf to Bay on picturesque southern Siesta Key, Island …
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 …
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 Key Home Rental
Experience luxury beachfront living with Siesta Key Home Rental. Choose from 3 unique properties, steps from the sand, offering relaxation, …
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 Inn
Welcome to Siesta Key Inn, your ideal Siesta Key vacation rental for a memorable getaway. Nestled just a short 5-minute …
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 …
Sunset Royale
Sunset Royale offers one and two bedroom condos fully equipped with all the amenities, including a full kitchen to make …
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 …
Gertrude Rentals
Find your perfect Siesta Key getaway with Gertrude Rentals!
Choose from 80+ professionally managed vacation rentals in Siesta Key's most desirable …
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 …
Stringer Management
Established in 1991, we are a 2nd generation family run business along with our “Team Stringer” representatives. Stringer Management has …
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, …
Jamaica Royale
Create the perfect setting for the type of vacation you deserve in one of our studio, one bedroom, or two …
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
Located in the heart of picturesque Siesta Key, Florida sits this award-winning nightly resort. White-sand quartz beaches combined with a …
Fisherman's Cove
Fisherman's Cove - Beachfront Vacation Rentals
Welcome to Fisherman's Cove, a premier collection of Gulf-front vacation rentals on Turtle Beach, Siesta …
Peppertree Bay
Private area on the famous, ultra white quartz sand of Crescent beach. Heated pools, fishing pier, barbecue, assigned parking, lighted …
El Presidente
We offer 39 spacious two and three bedroom fully furnished vacation rental condominiums right on the beautiful beach. Our friendly …
The Anchorage
While private beach access is included with your stay, we also have a wide variety of things to do onsite …
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 …
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 …
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 …
White Sands Village
Seven acres with fully equipped one and two bedroom condos on tropical grounds. Facilities include a heated pool, barbeque grills, …
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. …
Tropical Sands Accommodations
We are the largest vacation rental management company on Siesta Key! From studios to 9 bedrooms. Most units offer free …
Siesta 4 Rent
We offer Studios - 5 bedroom condos and homes on beautiful Siesta Key. All units are fully equipped, most directly …
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 …
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 …
Sea Spray Resort
Discover the new Sea Spray Resort - thoughtfully renovated and reopened in 2025. Steps from Siesta Beach and Siesta Key …
Siesta Gulf View
Siesta Gulf View is directly on world famous Siesta Beach, with its incredible sugar white crystal sands. Limited monthly Gulf …
Azul Siesta Key
Welcome to Azul Siesta Key, formerly The Cottages at Siesta Key, a refreshed coastal escape steps from the island’s soft …