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Sarasota, Florida Vacation Rentals

148 listings found
About Sarasota, Florida

Tropical breezes, island adventures and the most amazing white sandy beaches in southwest Florida, a Sarasota resort vacation is the one trip that defines a perfect vacation. With its prime location near the Gulf of Mexico, a Sarasota vacation rental offers an amazing array of water sports activities that include swimming, fishing, boating, and practically any extreme variation with wave runners, wind sailing and more. On land, your Sarasota rental is located near historic nature preserves and wildlife sanctuaries allowing you to experience the beauty of the region in an intimate setting. And with creative culinary options by international chefs along with shopping options that vary from boutique to high-end, a Sarasota resort vacation will fill your senses and tastes in ways you never thought possible.

Sarasota Resort Vacation Is a Cultural Experience

Right near the white sand, blue waters and the orange burst of bright sunshine, you are only minutes away from the aquatic action in your very own Sarasota condo rental on the mainland. In fact, staying at a Sarasota condo or vacation house in the city brings you close to many mainland activities and entertainment options while still in close proximity to beaches. Cultural enrichment is at every corner, with the famous John and Mable Ringling Museum of Art, the Sarasota Opera House and the Van Wezel Performing Arts Hall offering year round programming. Imagine a warm breezy walk from your Sarasota vacation rental right to the front door of a famous arts venue—perfect for a romance or a great way to bring the family together. Whether you choose a luxury house or a condominium in Sarasota, we have an amazing selection of intimate and plush accommodations to fit your specific need.

Surround Yourself in Nature near Your Sarasota Rental

Near your condominium in Sarasota or your Sarasota house rental, you can also explore the area’s beautiful natural surroundings on your Sarasota vacation. At Myakka State Park, you and your loved ones can become one with nature as your explore this extensive public park with lush, tropical landscaping. You can also take an airboat guided tour of the river or spend the day on hiking trails—all within close proximity to many Sarasota house rentals and the many charming Sarasota condos.

Gorgeous Golf Courses Surround Your Sarasota Rental

Speaking of beautiful surroundings, Sarasota boasts some of the most splendid golf courses in the region—many of which are located near cozy Sarasota vacation rentals. With the warm Gulf breeze welcoming you to the greens, a day on one of our award winning courses provides the perfect way to experience the weather and enjoy our year-round amazing temperatures beside your luxury condominium in Sarasota. Sports enthusiasts should also note that Sarasota is home to the spring training camp of the Baltimore Orioles—a great way to see a major league team prepping for the big game.

Fine Dining Only Minutes from Your Sarasota House rental

If fine dining is your leisure activity of choice, you will find a Sarasota condo rental or Sarasota house rental within minutes of some of the Gulf Coast’s finest array of international restaurants. From intimate chef-driven restaurants in Sarasota’s historic Towles Court art district to fine dining near Sarasota’s performing arts venues, a Sarasota vacation is one defined by good taste. From French and Italian cuisine to Tapas and fresh seafood options, fine dining begins on Florida’s Gulf Coast.

Luxuriate in Your Very Own Vacation House in Sarasota

If you want to get a taste of historic Sarasota, enjoy dynamic cultural opportunities and take in the urban amenities of a progressive Gulf Coast city only minutes from the world’s most beautiful beaches, a Sarasota condo or vacation house in Sarasota is the prime location for your next big trip. Check out the wonderful amenities of a Sarasota condo rental or find high-end luxury in your own vacation house in Sarasota and discover Southwest Florida’s secret hideaway resort.

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Rate & Availability Disclaimer
Base rates (EXCLUDING any applicable taxes, fees, and promotions) are displayed as provided by rental managers and are not guaranteed. Rates are based on the start date or arrival date selected in the search and may vary on subsequent days. Properties marked ‘Available’ or ‘Booked’ are done so based on information provided by the rental manager and are not guaranteed. For completed details (including minimum stay length, full availability information, approved arrival days and other booking rules for the property) select ‘Book Now” (on available properties) or ‘Check Availability’ (booked properties) to be directed to the rental manager’s website or click “Contact” to send them a specific request.

Ocean Sky | Pet Friendly Home in Sarasota w/ Private Heated Pool & Fire Pit!

Casamigos | West of the Trail - Private Home with Tiki Bar, Heated Pool, and Spa, Near Siesta Key!

Ventana Rosa | Beautiful Sarasota Home Near Siesta Key w/ Private Pool & Large Outdoor Space

The Pearl on the Bay | Luxury Water Front Home Near Siesta Key, Gorgeous Views & Private Pool!

Casa Leone | Pet Friendly Home on Siesta Key w/ Private Heated Pool & Putting Green!

Luna Nueva | Pet Friendly Home in Sarasota w/ Private Heated Pool & Screened-In Porch

Baydream Bungalow | Pet Friendly Home w/ Private Heated Screened-In Pool

Luna Flores | Pet Friendly Home in Sarasota w/ 2 Private Heated Pools & Screened-In Porches

Villa Las Flores | Pet Friendly Home in Sarasota w/ Private Heated Pool & Screened-In Porch

Palm Paradise | Pet Friendly Home on Siesta Key w/ Large Heated Private Pool & Outdoor Area!

Floritas Key | Pet Friendly Home on Siesta Key w/ Large Heated Private Pool & Outdoor Area!

New Listing! Siesta Dolce | Luxury Siesta Key Home w/ Private Heated Pool, Close To Beach!

Bay Isle Bliss | Pet Friendly Home w/ Private Pool & Walking Distance to Shell Beach

Hemingway House | Beautiful Traditional Home w/ Spacious Outdoor Dining Area & Lush Landscaping

New Listing! Mermaids Oasis | Private Pool, 5 Minute Walk to St. Armands Circle!

Coconut Cottage | Home on Lido Key w/ Private Heated Pool/Spa, Walk to Lido Beach & St. Armands!

New Listing! Manatee Cove | Waterfront Home on Lido Key, 30 Second Walk to St. Armands Circle!

Sunset Heaven | St Armands - Lido Key Home w/ Water Views, Dock Access, Private Heated Pool & Spa!

Coral Breeze | Siesta Home, Heated Pool & Spa, Minutes to Village and Beach!

New Listing! Sunburst Courtyard | Pet Friendly Waterfront Home, Walk to Siesta Key Beach & Village!

New Listing! The Birdhouse | Private Siesta Key Home w/ Heated Pool, Minutes Away From Beach!

New Listing | Pet Friendly Home on Siesta Key w/ Outdoor Patio & Private Screened-In Heated Pool!

Hidden Treasure | Located on Siesta Key w/ Private Heated Pool/Hot Tub & Spacious Outdoor Area

New Listing! Island Sol | Private Pool, Pet Friendly, Minutes from Siesta Beach

Bali Hai House | Luxury Waterfront Home on Siesta Key w/ Large Private Heated Pool & Outdoor Patio!

Blu Sky Cottage | Pet Friendly, Canal Front Home on Siesta Key w/ Private Heated Pool & Spa, Kayaks!

New Listing! Don't Be Salty | Gorgeous Modern Home w/ Private Heated Pool & Spa, Near Beach!

Villa De Paradisio | Waterfront Home w/ Private Pool, Fishing Dock, Close to Beach & Village!

The Sun Dial | Waterfront Home on Siesta Key w/ Private Pool & Large Backyard, Close to Beach!

Sophie's Quartier | Siesta Bundle, 2 Pet Friendly Waterfront Homes w/ 2 Private Pools, Near Village

Villa Champagne | Pet Friendly Waterfront Home w/ Private Pool & Spa, Close to Beach & Village!

Sophie's Cottage | Pet Friendly, Waterfront Home w/ Private Pool & Kayaks! Beach & Village Close!

Villa Castile | Pet Friendly Home on Siesta Key w/ Private Heated Pool, Walk to Beach & Village!

Isla Amor | Waterfront Home on Siesta Key w/ Private Heated Pool, Fire Pit, Walk to Beach!

Sand Dollar Cottage | Waterfront Home w/ Private Pool & Kayaks! Minutes to Siesta Key Beach!

Seas the Day | Canal Front Home on Siesta Key w/ Private Heated Pool & Kayaks, Walk to Beach!

Casa De Siesta | Pet Friendly Home In Siesta Village, Private Pool and Hot Tub, Walk to the Beach!

Villa Margarita | Pet Friendly Home In Siesta Village, Heated Pool and Hot Tub, Walk to the Beach!

Villa Fiesta | Pet Friendly Home In Siesta Village, Heated Pool and Hot Tub, Walk to the Beach!

Siesta Soul | Multilevel Home Located in Siesta Key Village w/ Private Pool, Fire Pit, Walk to Beach

The Big Kahuna | Luxury Pet Friendly Home on Siesta Key, 2 Heated Pools, Steps to Beach & Village!

Casa Mahalo | Pet Friendly Home on Siesta Key w/ Private Heated Pool, Steps to Beach & Village!

Casa Ohana | Pet Friendly Home on Siesta Key w/ Private Heated Pool, Steps to Beach & Village!

The Palms Cottage | Pet Friendly Home w/ Private Pool & Spa, Walking Distance to Siesta Key Beach!

The Hummingbird | Pet Friendly Home Located in Siesta Key Village w/ Private Pool, Walk to Beach!

Honeysuckle | Pet Friendly Home Located in Siesta Key Village w/ Heated Pool, Walk to Beach!

Lantana | Pet Friendly Home Located in Siesta Key Village w/ Heated Pool, Walk to Beach!

Mimosa | Pet Friendly Home Located in Siesta Key Village w/ Heated Pool, Walk to Beach!

Mandevilla | Pet Friendly Home Located in Siesta Key Village w/ Heated Pool, Walk to Beach!

Plumbago | Pet Friendly Home Located in Siesta Key Village w/ Heated Pool, Walk to Beach!

Vinca | Pet Friendly Home Located in Siesta Key Village w/ Heated Pool, Walk to Beach!

La Contento Casa | Pet Friendly, Waterfront Home on Siesta Key w/ Private Heated Pool & Kayaks!

Beach Walk Cottage | Pet Friendly Home on Palm Island, Private Pool, Ping Pong Table, Walk to Beach!

New Listing | Gulf Birdie | Waterfront Home on Siesta Key, w/ Private Heated Pool & Hot Tub!

Tropical Oasis | Luxury Home on Siesta Key w/ Private Heated Pool/ Spa, Steps to Beach & Village!

The Key Canal - Spacious Waterfront Home w/ Rooftop Deck, Walk to Siesta Beach & Village

Siesta Villa | Luxury Condo in Siesta Village w/ Heated Pool, Walking Distance to Beach & Village!

Latitude Adjustment | Waterfront Home w/ Private Heated Pool! Walk to Siesta Village & Beach!

Siesta Breeze Retreat | Walk to Beach, Siesta Village, Shared Pool!

At Sun Sea Terrace | Luxury Siesta Key Condo w/ Heated Pool, Short Walk to Beach and Village!

Sea Foam | Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!

Sea Angel | Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!

Sea Breeze | Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!

Sea Coast | Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!

The Beachy Keen | Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!

CJs on Siesta | Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!

The Coral Reef! | Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!

Sea Dream | Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!

Sea Escape | Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!

Sea Esta | Walking Distance to Siesta Key Beach & Village w/ Heated Pool & Outdoor Dining

Siesta Salt Life | Walking Distance to Siesta Key Beach & Village w/ Private Heated Pool!

Sea la Vie | Walking Distance to Siesta Key Beach & Village w/ Heated Pool & Outdoor Dining

Beach Palm Villa | Private Heated Pool, Fire Pit, & Spacious Outdoor Lounging Area

Caribbean Dream | Luxury Condo on Siesta Key w/ Heated Pool, Walking Distance to Beach & Village!

New Listing! Avanti Villa | Hot Tub, Walk to Siesta Beach and Village, Beach Views

Endless Views | Walking Distance To Siesta Key Beach + Village, Panoramic Views

Seaside Cottage | Pet Friendly Siesta Key Home w/ Private Pool, Across From Beach Access 9!

Peacock Villa | Spacious Outdoor Area, Cabana Room, Heated Pool, & Steps to Siesta Key Beach!

Monarch Villa | Ocean Views, Cabana Room, Heated Pool, & Steps to Siesta Key Beach!

Casa De Mariposa | Ocean Views, Spacious Balcony, Private Heated Pool, & Steps to Siesta Key Beach!

Siesta Sunset | Luxurious Beach Front Penthouse w/ Views of Gulf, Minutes to Siesta Key Village

Island Escape | Home on Siesta Key w/ Private Heated Pool & Ping Pong Table!

Beach Dream | Home w/ Ocean Views, 2 Private Pools, & Rooftop Lookout! Steps to Siesta Key Beach

Crystal Sands | Home w/ Ocean Views, Private Pool, & Rooftop Lookout! Steps to Siesta Key Beach

Silver Shore | Home w/ Ocean Views, Private Pool, & Rooftop Lookout! Steps to Siesta Key Beach

Admirals Watch | Ocean View w/ Spacious Balcony, Heated Pool, & Walking Distance to Siesta Key Beach

Villa Vista Mare | Gorgeous Home w/ Views of Gulf, Heated Pool, & Across From Siesta Key Beach!

Sandpiper Cottage | Pet Friendly Home in Sarasota w/ Private Pool, 2 Story Loft, Close to Siesta Key

The Abalone | Luxury Pet Friendly Home on Siesta Key, 2 Heated Pools, 2 Elevators, Steps to Beach!

Casa Junonia | Pet Friendly Home on Siesta Key w/ Private Heated Pool & Elevator, Steps to Beach!

Casa Stolida | Pet Friendly Home on Siesta Key w/ Private Heated Pool & Elevator, Steps to Beach!

The Nautilus | Luxury Pet Friendly Home on Siesta Key, 2 Heated Pools, 2 Elevators, Steps to Beach!

Casa Tegula | Pet Friendly Home on Siesta Key w/ Private Heated Pool & Elevator, Steps to Beach!

Casa Eulimia | Pet Friendly Home on Siesta Key w/ Private Heated Pool & Elevator, Steps to Beach!

The Conch | Luxury Pet Friendly Home on Siesta Key, 2 Heated Pools, 2 Elevators, Steps to Beach!

Casa Antilles | Pet Friendly Home on Siesta Key w/ Private Heated Pool & Elevator, Steps to Beach!

Casa Coquina | Pet Friendly Home on Siesta Key w/ Private Heated Pool & Elevator, Steps to Beach!

Casa Bella Vita | Luxury Home w/ Heated Pool, Ping Pong Table, & Walking Distance to Crescent Beach!

Casita Morning Star | Pet Friendly Home on Siesta Key, Heated Pool, Walk to Beach & South Village!

The Solaster | Pet Friendly Home on Siesta Key w/ 2 Heated Pools, Walk to Beach & South Village!

Fiesta Playa | Luxury Home on Siesta Key w/ Private Elevator, 2 Minute Walk to Crescent Beach!

Topsail Cottage | Luxury Home on Siesta Key w/ Heated Pool & Rooftop View of Gulf, Walk to Beach!

Casita Sun Star | Pet Friendly Home on Siesta Key, Heated Pool, Walk to Beach & South Village!

Crescent Cottage | Private Pool, Lounging Area, Short Walk to Crescent Beach

Sandy Rocks | Ultimate Bundle: 2 Private Pet Friendly Homes, 2 Private Heated Pools, Walk to Beach!

Sandy Seahorse Cottage | Pet Friendly Home on Siesta Key w/ Private Pool, Short Walk to Beach

Sandy Cabana | Pet Friendly Home on Siesta Key w/ Heated Pool, Short Walk to Beach!

Serenity Cottage | Multilevel Home on Siesta Key w/ Private Pool & Spa, Short Walk to Beach!

Seahorse Cabana | Pet Friendly Home on Siesta Key w/ Heated Pool, Short Walk to Beach!

Turtle Bay Hideaway | Large Pet Friendly Home on Siesta Key w/ Private Pool & Spa, Beach Access

Cozy 2BR Florida Home Near the Shore!

King Bed & Patio, Minutes to the Beach

Florida Retreat Nr Lakewood Ranch Sports Campus

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New Listing! | Front Row Seat | Luxury Beachfront Home Located On Anna Maria Island!

New Listing! | Beach a la Mode | Luxury Canal Front Home on Anna Maria Island!

New centrally located chic family home in Tampa

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