Mansion vacation rentals in Siesta Key

Htd Saltwater Pool- Near Beaches - 6bd/3ba

Relax in this stunning mid-century modern house near the beach with NEW saltwater pool with stone deck & splash pad/sun deck! Make your own childhood dreams come true for the kids with a backyard treehouse that is sure to make lifelong memories! This palm oasis is sure to please everyone! We have thought of everything, including all the vacation essentials for home, pool, & beach! Don't miss your chance to relax on America's favorite beaches at Anna Maria Island & Siesta Key- just minutes away!

Luxury villa 4 bdr with a heated pool (14guests)

Rare to find a luxury villa with a swimmable heated pool at the upscale district of North Port near a golf course. Very spacious (14 guests), high ceiling. Two empty lots on both sides of the property and a canal on the back guarantee full privacy. 2 minutes to Walmart and Publix. 10 minutes to Warm Mineral Spring. Close to Water park, Wellen park, Manasota, Siesta and others beaches. Very close to highways. The home is 2230 sq. ft. of living space. Fully furnished with high-end furniture.

Heated Pool Game Room & sleeps 18, 15min to Beach.

Step into a meticulously restored 1898 estate, where historic charm meets modern luxury. This expansive retreat boasts four king suites, a whimsical Harry Potter-themed game room, and a private carriage house. Unwind by the heated pool, enjoy cocktails at the outdoor bar under twinkling fairy lights, or explore nearby beaches and the vibrant Twin Dolphin Marina. Perfect for family reunions or celebratory getaways, this haven offers an unforgettable experience blending relaxation and adventure.

Florida Paradise Waterfront Home

Vacation in the lap of luxury with this spacious and unique waterfront home that was once featured on MTV Cribs! This gorgeous 5,000 sq ft home features 5 bedrooms, including two sleeper sofas in the large King + Queen suites to allow for more guests. 4.5 bathrooms and elevator. Entertain with a full bar, pool table, foosball, and shuffleboard table. Lounge and grill pool side on the massive deck over looking the water and breathtaking sunsets! Located just 15 mins from Apollo Beach.

Massive 6 BR/8BA All Suites, Pool Hot Tub Peloton

Massive 5000 Sq Ft Beach House just a short drive to the beach and steps from the bay! 6 Private Suites—each with a private ensuite bath—sleeps 20, perfect for multiple families. Enjoy an 85" TV Home Theater, Billiard Room, Game Room, Hot Tub, Peloton, & Heated Screened Pool with entertainment space. Dine together at the oversized custom-built 12-ft table. Plus, our backyard is professionally treated for mosquitoes! Minutes from top dining, shopping, and Anna Maria Island’s beaches!

Luxury Lemon Bay 4 BR villa w/ pool

This spacious 2156 square feet large and unique villa is set close to Manasota Beach and offers you 4 bedrooms and 3.5 bathrooms, a heated pool with a large barbecue area. You will find three bedrooms in the main house. Two king bed master suites and two single beds. Next, there is one separate bedroom with a queen size bed at the pool level (with its own entrance and en suite bathroom). The charging of EV is not allowed and an extra fee will be charged.

Designer 5BR for Groups | 10-Min to AMI

This inviting 5-bedroom, 3-bath home was designed and curated with families and groups in mind. Just 10 minutes from Anna Maria Island, enjoy walkable access to nearby beaches, local dining, and all the area has to offer. Additional amenities include a private heated pool, game room, ping pong, and family-friendly amenities to make traveling with little ones easier.

Stunning Sarasota Estate with Beautiful Pool

Newly renovated and spacious 4 bedroom home on a private and quiet 1 acre of land in the heart of Sarasota. Minutes from local restaurants, golf courses and shopping. 15 minutes to the beautiful Lido beach and 10 minutes to Downtown and the Marina. Fully secured fenced in yard and one of a kind backyard with a heated pool.

Pool, Hot Tub, Putting Green, 2 min walk to beach!

Experience the ultimate Florida getaway at #WeekendSuits, an exceptional 4-bedroom, 3.5-bath retreat nestled in the heart of Holmes Beach. Just a short block from Anna Maria Island's renowned gulf beaches, this meticulously appointed home combines outdoor living at its finest with sophisticated coastal comfort.