Vacation rentals with a pool in Treasure Island

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Top-rated rentals with a pool in Treasure Island

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favourite
An outdoor seating area is shown with a glass-top table surrounded by four blue chairs. Two charcoal grills are positioned nearby under palm trees, with a view of the water in the background. The screened cabana features a thatched roof, providing a relaxing atmosphere.
Condo in Treasure Island
4.9 out of 5 average rating, 184 reviews

Waterside Studio in the heart of TI, walk to beach

Location!!! This charming 2nd floor studio is located in the heart of legendary Treasure Island on the Intracoastal waterway of Boca Ciega Bay, only 3-7 min walk from the beautiful Gulf beaches, restaurants, shopping, and many great beach bars. Relax in the heated pool, have a cookout with the grills and screened waterfront cabana, complete with TV and minifridge, and watch the sunset or fish on one of two docks as dolphins frolic in the warm Gulf waters around you! Your perfect vacation awaits!

Top guest favourite
A well-lit living area features a round dining table surrounded by four white chairs. A comfortable sofa and armchair are positioned near large windows, offering views of the outdoors. Light-colored walls and soft furnishings enhance the bright, airy ambiance.
Condo in Treasure Island
4.91 out of 5 average rating, 129 reviews

2/2 Newly remodeled Beach Front - Sunset Vistas

Amenities/Location-Newly Remodeled Oceanview Condo with Balcony, Gorgeous Beach, Sleeps 6, king/master, queen/guest, queen sleeper, in unit washer/dryer, Smart 60- & 55-inch tv’s, cable, Wi-Fi, equipped kitchen, heated pool, kids pool, two jacuzzies, Tiki Bar, Cafe, rental bikes, Ping-Pong, Volleyball, Gym, Business Center, free covered parking, 5 day to monthly rentals. - Laundry detergent shampoo, conditioner and body wash, Beach Towels provided - 1/2 A MILE TO JOHNS PASS & No Resort Fees

Top guest favourite
An aerial view captures the waterfront community, highlighting the proximity to the beach and nearby amenities. Serene blue waters of the canal intertwine with the residential buildings, while the expansive shoreline stretches in the background, offering a picturesque setting for relaxation and exploration.
Condo in Treasure Island
4.98 out of 5 average rating, 151 reviews

Beach, dolphin/manatee sightings, fishing, sunsets

Welcome to the newly remodeled condo in the Heart of Treasure Island. This bright and modern retreat is perfect for relaxing and avoiding the crowds. Perfect location for beach lovers and wildlife watchers alike with waterfront views of the canal from the living room, kitchen and bedroom windows and beautiful sunsets. Just 2 blocks or a 5 minute walk to the beautiful white sandy beach and a few feet from the canal and heated pool. Visit nearby restaurants, John's Pass Boardwalk and live music.

Top guest favourite
An aerial view captures a multi-story condominium overlooking a beach. Lush palm trees surround a heated pool area, with docks lining the waterfront. The expansive coastline is visible in the background, highlighting the scenic proximity of beach and bay.
Condo in Treasure Island
4.99 out of 5 average rating, 212 reviews

Spectacular beach to bay views from this resort.

Our condo has spectacular water views from the Bay to the Beach. We have a large one of a kind kitchen that is unique to our resort, with granite counter tops, hardwood cabinets, and all stainless steel appliances. Everything you need to prepare a meal is provided along with basic spices and condiments, Coffee, creamer, and sugar. The master bedroom has a new king size bed and walk in closet with all beach gear also available for your use. We have 2 - 50" flat screen TV's with cable as well.

Top guest favourite
A well-maintained swimming pool is surrounded by palm trees and greenery, overlooking the intercoastal waterway. The clear blue water of the pool contrasts with the vibrant landscape, and a serene view of the water can be seen in the background.
Condo in Treasure Island
4.99 out of 5 average rating, 144 reviews

Treasure Island 1 BR condo intercoastal waterfront

Beautiful 1 BR 1 bath condo with awesome water view of the intercoastal located in Westwinds Waterfront Resort 800 square feet with large living area including 65 in tv, queen sofa sleeper, full kitchen, king bed in master. Short walk to beach of Treasure Island. Grocery store, restaurants and bars all within walking distance. The Resort has heated pool, two gas grills, elevators and 3 docks and peaceful area to just sit and look at the water. Boats up to 24’ welcome with reservation.

Guest favourite
An aerial view captures the coastline with sandy beaches meeting the gentle waves. The vibrant waterfront community features a mix of buildings and greenery, with beachgoers enjoying the open space. The location is highlighted by a marker indicating proximity to the water.
Condo in Treasure Island
4.92 out of 5 average rating, 119 reviews

Waterfront Condo With Pool and Multiple Views!

Enjoy the beach and the bay while staying in this upscale 3rd-floor condo unit just steps away from the beach! This beautiful unit offers 1 king bedroom plus 1 queen sleeper sofa. The 758 sq ft condo features a large waterfront pool with docks, outdoor grills, dining areas, free wifi, beach toys, and a full-size updated kitchen with everything you need for an enjoyable experience. Shops, restaurants, grocery stores, and entertainment are all nearby. Come enjoy paradise on Treasure Island!

Top guest favourite
A tranquil view captures the sandy shoreline meeting the calm waters of the Gulf, with gentle waves lapping at the beach. Lush palm trees are positioned in the foreground, while a small blue trash bin is nestled among the greenery. The sky features soft clouds, hinting at the day's potential.
Condo in Treasure Island
4.97 out of 5 average rating, 144 reviews

Beach Front Penthouse Riley's Retreat Island Inn

800 sq ft top floor condo with spectacular views of the Gulf of Mexico, Boca Ciega Bay, and the City. Located in the iconic Island Inn Beach Resort; step out of the lobby and onto the sand! Florida sunrises and sunsets are legendary, and you can enjoy both from your private top floor balcony. We offer one of the finest condo's in the building with the unique ability to enjoy North, South, East, and West vistas. This condo is unlike any other unit in the building--a must see!

Superhost
A modern four-story building is depicted, featuring balconies and large windows. The lush landscape is complemented by palm trees. A swimming pool is visible in the foreground, surrounded by sun loungers and shaded seating areas under blue umbrellas.
Condo in Treasure Island
4.85 out of 5 average rating, 359 reviews

Newest Beach Condo Resort in Treasure Island

Treasure Island has a new gem! Brand new large 2 bedroom condo, (992 sq ft,) directly on the beach. This unit has 2 bedrooms and 2 full bathrooms, as well as a pullout couch in the living room to comfortably accommodate 6 people. The open concept living area includes a full kitchen and a private balcony with retractable sliding doors. You might choose to sit on your balcony watching the sunset while reminiscing about your day or while watching the sky light up at sunrise.

Top guest favourite
An open-concept living area features a light-colored, patterned sofa paired with a wooden coffee table. A large flat-screen TV is mounted on the wall, and a serene window nook offers natural light, enhancing the coastal charm of the space.
Condo in Treasure Island
4.97 out of 5 average rating, 203 reviews

*Shore Thing* Walk to Beach | Intercoastal Views

🏖️ Shore Thing Condo 🏖️ Experience the ultimate blend of Sunset Bliss at this stylish Treasure Island retreat. Just steps from powdery sands, ocean breezes and breathtaking sunsets. Keep an eye out for local wildlife as dolphins and manatees glide by. Inside, enjoy coastal vibes featuring modern beachy interiors. Whether you are preparing a meal in the luxury kitchen or diving into the intercoastal heated pool, my service ensures your comfort always comes first.

Top guest favourite
An inviting living area features a light gray sofa and a round white coffee table. Large glass doors open to a private balcony with unobstructed views of the Gulf of Mexico, creating a seamless connection with the beachfront landscape.
Apartment in Treasure Island
4.93 out of 5 average rating, 160 reviews

Beachfront Condo w/ Ocean View - Newly Renovated!

Newly renovated, 4th floor beachfront condo with a private balcony overlooking the gulf on Treasure Island Beach within walking distance to beaches, onsite pool, bars, and restaurants. View the sunset from your condo where you can relax in a queen size bed, full size sofa bed, and single fold up cot. Inside is a combo living/dining area and fully equipped kitchen, surrounded by beautiful furnishings and art.

Guest favourite
Aerial view of a two-story condo building located beside a swimming pool, surrounded by palm trees. The pristine beach and the Gulf of Mexico are visible in the background, showcasing calm waters and distant beachgoers.
Condo in Treasure Island
4.91 out of 5 average rating, 184 reviews

Seaside Condo: 2bed/2bath beach condo on the water

This beautiful 2bed/2bath condo is right across from the beach! Located on the waters of the Gulf of Mexico, it is fully equipped with all the amenities to make your stay comfortable- heated pool, docks to fish, grills, laundry on each floor, and spacious patio area. The grocery store (Publix) is a short walk and there are plenty of restaurants, bars, and water activities nearby!

Guest favourite
A spacious balcony features a round table surrounded by four wicker chairs. Lush palm trees provide shade, while a clear view of the ocean and beach is visible in the background, creating a relaxing outdoor space.
Condo in Madeira Beach
4.87 out of 5 average rating, 106 reviews

Beach Place Bliss on Madeira Beach by John's Pass

This is a spacious 1400 square foot ocean front corner condo. The balcony has a great full view of the beach. There have been many new updates to the condo. New floor tilling was installed, along with the bathroom showers and bedroom furniture. Enjoy great views of the beach and beautiful sunsets from the privacy of your first floor balcony.

Popular amenities for Treasure Island rentals with a pool

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Quick stats about vacation rentals with a pool in Treasure Island

  • Total vacation rentals

    Explore 1,510 vacation rentals in Treasure Island

  • Nightly prices starting at

    Treasure Island vacation rentals start at $70 CAD per night before taxes and fees

  • Verified guest reviews

    Over 40,590 verified reviews to help you choose

  • Family-friendly vacation rentals

    1,010 properties offer extra space and kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 190 rentals that welcome pets

  • Rentals with dedicated workspaces

    950 properties have a dedicated workspace

  • Wifi availability

    1,480 of Treasure Island vacation rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Treasure Island rentals

  • 4.7 Average rating

    Treasure Island stays receive an average rating of 4.7 out of 5 from guests

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