Hotels & Lodging

1045 Lemon Bay Dr

528 S Polk Dr

317 Canal Rd

Siesta Key: 2 Bedroom, 3 Beds, 2.5 Bath; Duplex with Pool Vacation Rental Across the street from the #1 Beach in the U.S. Siesta Key Beach is commonly rated the # 1 beach in the United States for good reason! With its soft, powdery white sand, huge 8-mile stretch of beach, and constant activity in and around Siesta Key itself, there are many reasons to fall in love with Siesta Key.

121 Cedar St

From the Beach to the Bay, Midnight Cove offers Premium, Family-Friendly (OneWeek Minimum Stay) Condominium and Townhouse Accommodations in the Heart of Beautiful Siesta Key on Crescent Beach! Our luxury two and three bedroom condominium and townhouse vacation rentals are individually owned, tastefully decorated, and furnished with all the conveniences of home to make your stay in paradise completely stress-free (we also have a 4BR beachfront townhome that sleeps 8).

Midnight Cove II, not to be confused with Midnight Cove is a condo complex with a walkway to Crescent Beach Public Access #12. Each of our 146 units are individually owned, and the property boasts a heated pool, tennis/pickleball courts, basketball court, bike racks, grilling/picnic area, fitness center and a laundry room. We require a minimum stay of 7 nights. We are not pet friendly with the exception of owners and they can have 1 medium sized pet.

16 S Orange Ave

5247 Calle Menorca

Discover the perfect getaway at our spacious North Port home! With three cozy bedrooms, two modern bathrooms, and six comfortable beds, there’s plenty of space for families, groups, or friends to relax and unwind. The home features four thoughtfully designed rooms, providing a welcoming atmosphere for guests of all ages. Enjoy a fully equipped kitchen, inviting living spaces, and a private outdoor area ideal for soaking up the Florida sunshine. Our convenient North Port location puts you close to beaches, golf courses, shopping, and local dining. For those seeking extra relaxation, we offer optional in-house spa massages and wellness treatments to make your stay even more memorable. Book your stay at this property today!

Enjoy a stylish experience at this centrally located place in the heart of the Rosemary District in Sarasota. It's a place to marvel, hit the nearby gym, enjoy a roadside coffee, or head to the boutique shops nearby. Downtown Sarasota (Main Street) & Bayfront & Whole Foods are just two blocks away! This vacation rental is also available for sale — contact the owner for details.

Osprey Harbor Village is a private, luxury waterfront villa at the end of Blackburn Point Road in Osprey, FL — inside a gated marina community with direct Intracoastal frontage. Guests enjoy a private dock, kayak launch, and boater's access to Little Sarasota Bay, plus resort-style amenities including a state-of-the-art gym, sauna, and spa. Minutes from Casey Key, Nokomis Beach, and Sarasota's best golf, dining, and cultural attractions. Available for luxury seasonal and short-term stays (30 day min)— inquire directly for availability and rates.

Peaks & Palms is a small family operated vacation rental group which specializes in personal service. When you call, we answer; when you message, we respond quickly. Avoid the big, impersonal rental companies and check us out!

Palm Villa is a cozy, tropical vacation rental home in Venice, Florida which has a fenced yard and is pet friendly

Park Place Properties provides professional short-term rental and Airbnb management in Sarasota, Siesta Key, Lido Key, Longboat Key, and Bradenton. We help vacation rental property owners maximize revenue through dynamic pricing, multi-platform listing on Airbnb, VRBO, and Booking.com, expert guest vetting, cleaning coordination, and full-service maintenance. Our Sarasota owners enjoy hands-off management, transparent reporting, and a dedicated local team. Whether you own a beachfront condo near Siesta Key or a vacation home in Sarasota, we're here to grow your investment. Contact us for a free STR revenue analysis.

Peppertree Bay is situated directly on the Gulf of Mexico with warm, turquoise water and famous white sand beaches. Dr. Beach rated Siesta Key Beach the best in America, and our island paradise has been among the top travel destinations in Florida for years. When you stay in our Siesta Key vacation rentals, you’ll be greeted with breathtaking waterfront views in a private beach with cooling tropical breezes and lush tropical gardens.

For more than 35 years, RVA Resort Vacations has been the premier choice for professionally managed rentals along Florida's Gulf Coast. Our extensive collection features beachfront condos, waterfront homes, and luxury villas spanning Longboat Key, Siesta Key, and beyond. Whether you desire a family retreat or a romantic escape, our dedicated team is committed to finding your ideal home away from home. We provide exceptional customer service and meticulously maintained properties, ensuring a seamless and memorable experience from booking to departure. Discover the perfect vacation rental and create lasting memories with RVA.

1960 Stickney Point Rd Ste 206

2 Bed, One Bath Top Floor Condo overlooking Siesta Key Beach Relax and enjoy spectacular Florida sunsets overlooking world famous Siesta Key Beach. This upscale, coastal design condo comfortably accommodates 6 and features a full kitchen and a comfortable living room overlooking a large, private screened balcony.

Siesta Key Beach Rental

Whether you are traveling for work or pleasure, let our vacation homes be the place you select to spend your time relaxing on the warm sunny beaches, fishing, boating or exploring the surrounding areas. We offer several homes in the area. Contact us for availability or visit our site. We have 2 homes available, one is Venice and another in Nokomis. Both clean and remodeled housing up to 12 people each. Please contact us for availability. Video walkthrough on YouTube

Vacation Rental Siesta Key Beach Sea Club 5B

Siesta Key Sea Club II is the perfect place for your vacation! In a gated complex, besides access to the #1 beach in the USA, there is a perfectly heated swimming pool, unbelievable fishing, a relaxed environment, a beautiful lawn to lounge on by the Intracoastal waterway, boating, parasailing and lots more. Chill out by the Intracoastal and you may see a pod of dolphin swim by, or a manatee and calf! In the evening, head out to the beach to see the sunset or Sunday evenings, catch the Siesta Key drum circle. Looking for more to do – head down to Caspersen beach to find some fossilized shark’s teeth. Rainy day – visit The Ringling museum (free on Mondays). What do you do in the evenings – Siesta Key Nightlife.

Siesta Key Sea Club II is the perfect place for your vacation! In a gated complex, besides access to the #1 beach in the USA, there is a perfectly heated swimming pool, unbelievable fishing, a relaxed environment, a beautiful lawn to lounge on by the Intracoastal waterway, boating, parasailing and lots more. Chill out by the Intracoastal and you may see a pod of dolphin swim by, or a manatee and calf! In the evening, head out to the beach to see the sunset or Sunday evenings, catch the Siesta Key drum circle. Looking for more to do – head down to Caspersen beach to find some fossilized shark’s teeth. Rainy day – visit The Ringling museum (free on Mondays). What do you do in the evenings – Siesta Key Nightlife.

Sarasota

Discover your perfect escape with Siesta 4 Rent, your premier gateway to unforgettable Siesta Key vacations since 1997. We offer a curated collection of exquisite condos, charming villas, and spacious homes nestled across beautiful Siesta Key, Florida. As a dedicated vacation home and property management company, we specialize in connecting you with the ideal rental to create lasting memories on the Gulf of Mexico. Experience the magic of Siesta Key using Siesta 4 Rent.

Vacation home rentals in Siesta Key, FL

Book a stay at our pet friendly bungalows on Siesta Key! Each home rental has a private yard, 5 minute walk to #1 Siesta Beach and Village. From Studios to more. Especially great deal for longterm or seasonal renters, offering weekly, monthly, and yearly stays!

1138 Windsong Ln

Siesta Key information portal including vacation rentals, Restaurants, Bars, markets, shops, beach rentals, beaches, parking information to assist your Siesta Key experience.

524 Beach Rd

Siesta Key Beach Florida Vacation Rentals

1009 W Peppertree Dr

6312 Midnight Pass Rd

Condo Vacation Rental, 1100 Sq Ft. , 2 Bedroom, 2 Full Bath, Sleeps 6, The Palm Bay Club

We have been doing vacation rental business on Siesta Key for 30 years. As a vacationer, we know you want a clean and cozy beach home for your vacation time with family and friends. Being close to the beach and close to the Village are something we specialize in. Our cozy vacation rentals make you feel at home and comfortable. As a potential or current owner of your own vacation home that you would like to rent...we can discuss all options of our services. Let the Beaching Fun Begin!!

5049 Ocean Blvd

The Salty Starfish is a beautifully decorated 2-bedroom villa located directly on the #1 beach in the USA. Sandy toes and stunning ocean views, a perfect spot for relaxation, just steps away from pristine white sands.

Enjoy the best of both worlds during your Florida vacation in this cozy, tranquil oasis located on beautiful Siesta Key. Our newly-upgraded condo is a quiet escape nestled amid lush tropical landscaping and is ideally situated within steps from both bay and gulf: just a 3 minute stroll to your private beach on Siesta Key (ranked #2 among America’s Best Beaches by Dr. Beach). You simply need a towel, a cool drink and some sun screen because the beach attendant will do the rest, including pulling up chairs and installing an umbrella for you! With some of the finest, whitest sand in the world, this beach is a magnet for shell collectors.

Siesta Key Vacation Rental

6145 Midnight Pass Rd E7

Straightforward beachfront condos with kitchens, plus a deck, BBQs & free parking.

Seven apartment vacation rental apartments with king-size beds in all bedroom areas and adjoining doors on each side of our two-bedroom/two-bath vacation rentals allow a two-bedroom/two-bath to expand to a three/bed-room/three-bath or a four-bedroom/four-bath suite. We offer daily, weekly and monthly availability with heated pool and spa plus an incredible barbecue for our guests to use. Across from Siesta Key Beach Access #7 on the Gulf of America and one block from the tropical Village of Siesta Key. Property manager on duty daily and will assist you with information on Siesta Key and Sarasota.

Siesta Villa Coralline is a stand-alone single story villa located in the beautiful community of Polynesian Gardens. Villa Coralline has been designed & decorated as an upscale beach cottage featuring two bedrooms, one with a King bed and the second with two twins. The villa’s tropical beach theme is displayed throughout the home offering a true connection between the Siesta Key atmosphere and the comforts of home. Enjoy the private outdoor space provided in the backyard of the home including a grill, dining table with umbrella as cover, lounge chairs, and the tropical plants that surround the area.

We’re a family-loving couple from Connecticut who first fell in love with Siesta Key on our honeymoon. Years later, with five kids, our passion for this magical place has only grown. Inspired by our family experiences and countless cherished memories here, we’ve poured our hearts into creating vacation rentals that feel just like home. We’ve thoughtfully equipped our rentals with all the necessities to ensure a comfortable and hassle-free stay, hoping to make your visit as special as our many trips here have been for us. We look forward to welcoming you and sharing the charm of Siesta Key!

6301 Yellow Wood Pl

What an amazing property at an amazing value. Siesta Key Village is literally in your back yard. This vacation home is located in the heart of Siesta Key, yet just far enough away that you still have your privacy. The home also has 2 soaking pools, wood deck and 2 private jacuzzis Hang out on the deck or just soak away as you listen to the sounds of music and fun from Siesta Key Village. When you're rested and ready to enjoy Siesta Key, the beach and the Village are both just literally steps away. When you're done for the day, walk back into the home and enjoy the large living room with ample seating and watch some TV or use the Free WiFi. Feel free to take a night off from eating out at one of the fantastic restaurants in your backyard.

Beautiful custom built homes with private pools located between Venice, Englewood and Port Charlotte within minutes to beaches, shopping, restaurants and sports facilities, which are some of the best that Florida has to offer.