Holiday rentals with a hot tub in Bayshore Gardens

Mediterranean-Type Waterfront w/Pool-Saltwater Spa

Kick back in this Scent of Serenity Retreat. This 3-Level Private 2-Bedroom/1 Bath apartment/loft sleeps up to 5 guests. Pool-Saltwater Spa. Recreation Rm. Shared Laundry Rm in bldg. Level 1: Twin Bed sleeps 1 Lev. 2: Master Queen Bed for 2; Lv Rm: Futon Sleeps 1 ; Air mattress sleeps 1 Lev.3-Observation/Yoga Rm. Spiral Staircase. No wheelchair access. Not suitable for kids under 12. 10mins from SRQ. Botanical gardens, shopping, restaurants - 1-2 mi. Beaches w/Free parking 9 mi away.

AMI/IMG/Boat/Bikes/Golf/Hottub/Kayak/Beach/pool

Welcome to the Paradise Fun House, the ultimate spot for your dream bash! Our Airbnb oasis is packed with tons of fun and activities for an epic stay. Cruise around on free bikes or kayaks, fish with top-notch gear, challenge friends to mini-golf, chill in the hot tub, or enjoy our game collection. Golf clubs and beach gear are ready to roll. Our spacious layout is perfect for partying all night long. Book now for the ultimate fun or relaxing experience! Boat/Dog-sitting/cleaning are available

Beach House with jacuzzi near AnnaMariaIsland

Welcome to the peaceful Gulf Trail Ranches community,located just 8miles from AnnaMariaIsland, with easy access to IMG and restaurants.This 2bed/2bath home offers a remodeled kitchen with stainless steel appliances, solid surface countertops, and a built-in breakfast bar.The spacious family room is equipped with a built-in bar for enjoying music,a vending machine stocked with drinks and snacks for your convenience, a fenced backyard with a gas grill and hot tub for a pleasant and relaxing stay.

The Florida Rooms

NEW POOL/SPA. Just 10 minutes from the beach, The Florida Rooms is a 3BR, 2BA retreat with NEW RESORT POOL & SPA, outdoor dining and living space, premium beds, rain showers, a full kitchen, and dining for 8. Extra sleeping includes a queen sofa bed and Pack ’n Play. Enjoy a pool table, ping-pong, board games, outdoor string lights, and a fire pit. We include beach gear—chairs, towels, umbrella, and wagon—for easy fun in the sun. Comfort, charm, and convenience await! Pool/spa heating included!

Manatee Cove: Waterfront Oasis w/GameRoom &HotTub

Welcome to Your Private Waterfront Oasis! This spacious home on a serene canal off Sarasota Bay features 3 bedrooms, 2 bathrooms & a HUGE climate-controlled game room! Enjoy direct water access for fishing, canoeing, kayaking and spotting manatees. Just 7 minutes from the airport & 15 minutes from Sarasota, you’ll have access to beautiful beaches like Siesta Key & Anna Maria Island. Offering free WiFi, BBQ grill & firepit, this retreat is perfect for families seeking relaxation & adventure!

Stylish 6 Bed Pool Home with Golf Simulator & Spa

Experience ultimate Florida luxury at our 6-bedroom, 4-bathroom Bradenton home, fully remodeled for your perfect staycation. Enjoy a heated saltwater pool, spa, outdoor kitchen, and bar with granite counters, ice maker, and fridge. Nestled at the end of a private drive, this paradise offers a golf simulator, putting green, and cornhole court. Centrally located yet secluded, it comfortably sleeps 12. Non-smoking and meticulously clean, this is your dream getaway for relaxation and fun.

5BR/4BA |Pool & Spa + Pickleball, Golf View

Welcome to Picasa by Stayawhilewithus — a Mediterranean-style 5BR/4BA golf-front retreat, on over an acre in one of Sarasota’s most desirable locations. Minutes to Siesta & Lido Key Beaches, Downtown Sarasota, St. Armands’ Circle, and SRQ. Enjoy a resort backyard with a resurfaced heated pool & spa (in Oct. 2025), a pickleball court, and a fire pit, in addition to elegant interiors with a chef’s kitchen, game room, and spacious bedrooms for families, golf groups, and wedding guests.

Exquisite modern home with pool - 10 min to beach

A beautiful modern home 10 min to Anna Maria Island and the beach with breathtaking amenities in Bradenton Florida. This 3 bedrooms, 2 bathrooms property is appointed with exquisite finishes and furniture throughout, heating and cooling pool, hot tub, large patio with lounge chair, complimentary bicycles and beach chairs, sonos system, outdoor BBQ and much more. Additional Housekeeping can be provided at an extra cost. Please contact the Property Manager for more information.

Tipsy Flamingo | POOL • HOT TUB • FIRE PIT • GAMES

Dive into the curious home of Tipsy Flamingo. The tropical fever dream you didn’t know you needed! Stay in a historic home bursting with fluorescent colors, a pink-tastic Flamingo Suite, a wild Jungle Room, and a chill coastal Surf Den. Outside, swing under the pergola, battle it out in giant chess, soak in the hot tub, lounge by the fire pit, and float in the sparkling pool on your honorary pink flamingo throne. Pure fun, pure vibes, pure madness! 🦩

Palmas de Lucia w/Hot Tub+5mi to Beach, Near IMG!

Discover comfort and style in this modern, spacious, and recently renovated house, perfectly located in the heart of the area. Beautiful beaches like Cortez, Coquina, Holmes, and Anna Maria Island are just 12 minutes away. Sarasota Airport, IMG Academy, art galleries, Lido Key, Longboat Key, museums, theaters, Marie Selby Botanical Garden, and Marina Jacks are all within 15–20 minutes. Disney World Orlando is only a 2-hour drive!

Sweet Retreat at Shorewalk!

Bring the whole family to this great place with lots of room for fun. A spacious 2 bedroom, 2 bathroom condo on the second floor, newly renovated and fully equipped, is within walking distance of supermarkets, restaurants, the cinema, and bowling. Whether you are a single family on vacation, a couple enjoying a weekend getaway, or a sports team in training, we have you covered. Stay with us and enjoy all the comforts of home!

A case of paradise

Catch a case of paradise and forget all your worries in this newly renovated three-bedroom home located in a quiet family friendly neighborhood. Only minutes away from beautiful Anna Maria Island, IMG and Sarasota airport. Enjoy a relaxing soak in the pool spa. Restaurants & shopping are minutes from the home. Have fun playing pool and enjoy the evening watching a movie with surround sound on your favorite app.