Vacation rentals with a pool in Whitney Beach

Waterfront, Heated Pool, Elevator, Fire Pit, Dock

Escape to The Blue Ark, a 3-story home inspired by Noah’s Ark. Families will love this peaceful retreat, blending luxury and comfort. Discover the island's only natural lagoon, boasting stunning views, manatee and occasional dolphin sightings! Unwind by the heated pool, fish from the dock, or take an easy 4-5 minute walk to the beach. End the day with a drink by the fire pit on the top deck, watching the sunset. The Blue Ark has an elevator, 3 bedrooms + extra sleep space, 8 beds and 4.5 baths.

Guest House with Hot tub & Heated Pool

Welcome to your serene retreat in sunny Florida! This beautifully finished 1-bedroom, 2-bathroom mother-in-law suite offers luxury, comfort, and privacy. With a heated pool and hot tub, we offer year round outdoor relaxation. Step into your own private oasis with a separate entrance and secluded patio, ideal for morning coffee or evening relaxation. Located in a quiet neighborhood backing up to a protected preserve, offering peace and natural beauty. Beach gear provided for easy beach days.

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!

Waterfront/ Sunsets/ Heated Pool/ Tiki Bar/ Dock

Welcome to The Tiki Retreat, Your Waterfront Oasis on Boca Ciega Bay!
Step into a bright, coastal 3 bedroom home where relaxing waterfront living meets vibrant tropical vibes. Enjoy stunning views, a private dock, a heated salt water pool, and your private tiki bar all set against the backdrop of beautiful Boca Ciega Bay, home to dolphins, manatees, and an array of wildlife. This spot has everything you need for an unforgettable stay. Feel free to bring your family pet (with pre-approval)

Island Time!

This sublime oceanfront studio is directly on the pristine white sands and serene blue waters of the Gulf of Mexico in Longboat Key, Florida! On the second floor, overlooking the heated pool and ocean, this dreamy studio condo is optimal for sunset viewing from a private lanai. Take a 30-second walk to the pool and secluded beach. Enjoy a relaxing vacation at our peaceful condo at The Beach at Longboat Key Resort! To see all four of our listings, click on my Host photo and scroll down...!

Sapphire Shores Muse | 2 Bed 3 Bath | Luxe Pool

Welcome to Sapphire Shores Muse, a stylish, fully-furnished retreat perfect for 30+ day stays. Located minutes from Siesta Key and downtown Sarasota, this upscale home offers a private pool, shaded lounge, and outdoor dining—ideal for unwinding after work. Inside, enjoy a chef’s kitchen, smart TVs, fast Wi-Fi, and serene bedrooms with luxe linens. Perfect for corporate stays, traveling nurses, snowbirds, local renovations and relocations. Experience Sarasota in comfort and style—book now!

New Modern on Beach Longboat Key (5 steps to Sand)

Newly renovated (November 2025) modern first floor condo literally five steps away from the sand walking outside from the lanai. One bedroom /One bath King bed in Primary Queen sleeper sofa in living room Key code entrance Free parking Heated Swimming pool on site Free Beach loungers on the beach Paid laundry machines on site Mid Island next to everything WiFi, cable, free parking Usually 7 night minimum Bring your toothbrush and bathing suite and prepare to unwind and relax!!!!

Stylish Pool Home 4BR Near Siesta Key "Palm Noir"

Welcome to Palm Noir, a brand-new modern luxury retreat in Sarasota just 12 minutes from Siesta Key Beach and 9 minutes from Downtown. This stunning pool home features soaring ceilings, impact windows and doors, designer finishes, luxury furnishings, bright open living spaces, and a private heated pool with spa. Enjoy premium bedding, fresh towels, a fully equipped kitchen, outdoor dining, lounge seating, and everything needed for the perfect family vacation or group getaway.

4 BR Pool Home | Sand Volleyball | Near AMI & IMG

Escape to Two Palms, a spacious 4-bedroom, 3-bath retreat in Bradenton, Florida. Perfectly located just minutes from the sugar-sand beaches of Anna Maria Island. Designed with comfort and relaxation in mind, this home offers everything you need for a memorable getaway. Step inside to an open-concept living space filled with natural light and plenty of space to unwind. Outside, enjoy a private salt-water pool and a beach sand backyard featuring a sand volleyball court.

Casa Noir | POOL • BBQ • FIRE PIT • GAMES • VIBES

Welcome to Casa Noir ! Your private, photoshoot worthy retreat! Lounge by the sparkling pool beneath the angel-wing mural, unwind on the swing daybed by the fire pit, or level up your stay with air hockey, arcade games, and a bike workout in screened in lanai while you watch the kids in the pool. Every corner is designed for fun, style, and that perfect photo moment for the Gram. No other stay vibes quite like this one!

Your DreamOasisAwaits: SiestaKeyEscape with Pool!

Welcome to your dream oasis near the world-famous Siesta Key! ✨ This immaculate 2BD/2BA home is a true coastal gem, offering a serene retreat with stylish design and luxurious amenities. Just 1 mile from the sugar-white sands of Siesta Key Beach, this home provides the perfect blend of comfort and convenience—an ideal spot to embrace relaxed Florida living at its finest. 🌴

New! Heated Pool~Steps to the Beach/Shops~Starfish

🌴 Villa #6 Starfish – Just 2 mins from Holmes Beach! 🐚 This 1BR/1BA villa features a king bed, queen sleeper sofa 🛏️, shared heated pool 🏊‍♂️, BBQ 🍔, dog-friendly 🐶, and lush tropical surroundings 🌺. Walk to shops, restaurants, and trolley 🚎. Washer/dryer, 1 parking space, and all the comforts for a perfect Anna Maria Island getaway 🌅.