Vacation rentals with a pool in Madeira Beach

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Top-rated rentals with a pool in Madeira Beach

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

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Guest favorite

Home in Seminole

4.87 out of 5 average rating, 259 reviews

⭐️Ultimate Vacation Home🌴Tropical Heated Pool Oasis

🌴 4min to the beach! Over 200 great reviews from guests! 🕶 Huge and gorgeous 4 bedroom home. Living, Dining, AND family room with pool table! Fully equipped kitchen. 🦋⛱PRIVATE tropical outdoor area with sparkling large private HEATED pool, lounging areas, outdoor grill, FIRE PIT! ⛹️‍♂️Basketball on the driveway! If your looking for vacation home here it is! 🏖Minutes away beaches! Beach chairs and beach towels provided. Experience the charm of Florida in a home you will want to call your own

Guest favorite

Home in St. Petersburg

4.99 out of 5 average rating, 68 reviews

Remodeled pool cottage, just minutes from beaches

Relax by our cocktail pool in this recently remodeled guest cottage that is just minutes from the Sun Coast beaches. You will find our cottage is fully equipped and has everything you'll need for a quick getaway or an extended stay. The back door opens up to the patio and the lush, tropically landscaped backyard pool area. 5-minute drive to St Pete Beach, 7 to Treasure Island. Uber, Lyft or ride the SunRunner shuttle, and forget about the hassle and expense of beach parking. We are pet-friendly!

Guest favorite

Tiny home in Dunedin

4.96 out of 5 average rating, 117 reviews

2 Bedroom Luxury Tiny Home with Pool "Sunny"

Fabulous newly built luxury tiny home in the heart of Downtown Dunedin! This charming 2 bedroom 1 bath home has everything you need for a perfect stay in our perfect little town. This home has an upstairs loft with King and Queen beds at opposite ends. Steps from all the best restaurants, breweries, shops and activities in Dunedin. Voted one of the best walking towns in America! Short drive to beaches! Or simply stay home and chill by the pool that's great too! This location can't be beat!!

Guest favorite

Home in St. Petersburg

4.95 out of 5 average rating, 200 reviews

Stunning Home with TWO Pool Cabanas+Guest Bungalow

A 6 min. drive to Madeira Beach and miles and miles of beach coast. Stunning pool home with TWO poolside cabanas and a brand NEW poolside guest bungalow.HOME SLEEPS UP TO 14 GUESTS! Fully renovated home with 3 full bathrooms. Wifi and 8 smart televisions. Professionally designed and decorated home in a family neighborhood near dining, shopping, Walmart and beaches! This home is professionally and immaculately cleaned before every guest. Heated pool OPTION is available for additional cost.

Guest favorite

Condo in Clearwater

4.95 out of 5 average rating, 112 reviews

POOL VIEW IN A MODERN CONDO - Feel at Home

For your best vacation, welcome to stay in our newly renovated and tastefully decorated condo for having a relaxed vacation ! Family with kids, young retired or just couples who want to spend romantic moments, everybody is welcome.The condo is located in a beautiful gated community, 10 min. by car from Clearwater Beach, voted # 1 beach in U.S. in 2013 and 2018. You can enjoy a large, beautiful heated swimming pool with salt water, a barbecue area, fitness center and an elegant clubhouse.

Guest favorite

Home in St. Petersburg

4.91 out of 5 average rating, 131 reviews

Heated Pool and hot tub luxury vacation house

Spend your vacation in luxury! The hot tub and heated swimming pool are perfect for a family vacation or a couples' retreat. In winter we keep the pool temperature at 85 degrees. Enjoy the stylish furniture, a huge luxurious master suite with a large walk-in closet and work desk, a fully equipped kitchen and all the extras you would expect at the resorts. The living room features a 75’ TV! Short drive to Madeira Beach and Treasure Island. Small parties are allowed. A lot of parking space.

Superhost

Rental unit in Clearwater Beach

4.76 out of 5 average rating, 128 reviews

☀Pool✔ Beach✔ Self Checkin✔ Free Parking✔

No hidden fees! No complicated checkout instructions! We make it easy for our guests. ☞ 2 min walk to the beach ☞ Free parking ☞ Heated pool ☞ AC ☞ Self check-in We provide essentials (linen, towels, toilet paper, shampoo, soap, etc.) at the beginning of your stay. We recommend getting more supplies for more extended stays. 648 Poinsettia Ave Clearwater Beach 33767 Location, location, location! 500 feet to the beach 500 feet to a park and playground 0.2 mile to public tennis courts

Guest favorite

Home in Palm Harbor

4.97 out of 5 average rating, 131 reviews

Tropical Getaway w/Heated Pool & King Beds

Welcome to our “sun-kissed” get-away in beautiful, conveniently located, Palm Harbor, FL. In less than 10 minutes you can find yourself sitting on the shore of one of our award-winning white sandy beaches or teeing off at a pristine golf course, and only 30 minutes from Tampa attractions. There is plenty of space to sleep 6 very comfortably, a beautiful bird caged pool and outdoor seating/lounging, BBQ grill, and fun for everyone. Come and enjoy...you just might not want to leave!

Superhost

Home in Largo

4.87 out of 5 average rating, 220 reviews

Salt Water Pool&Hot Tub 4mi from Gulf Beach-slps 8

Perfect for your next FL vacation! This trendy home is equipped with full kitchen, coffee bar, ivy wall/neon sign with Polaroid photo booth for your photo ops, 3 smart TVs, indoor golf putting green, Tempur pedic mattresses, & small reading nook. Outside presents a large in ground Salt Water Pool and Hot Tub, Day bed under palm trees, Bistro set for morning coffee, &fire pit w/ high privacy fence tucked into a quiet neighborhood just 4 mi from gulf beaches!

Guest favorite

Home in Indian Rocks Beach

4.95 out of 5 average rating, 63 reviews

Stunning Waterfront Pool Home Walk to Beach

Relax at the Twin Dolphins luxury pool home, your five star vacation paradise! Bright and open freshly remodeled and ready for your visit. Large heated private pool offers fun for everyone. Well equipped and actively managed, so you are well cared for. This property offers the best of pool and beach living at a fraction of resort prices. You rent the entire property, 4 bedrooms, 3 baths, a large rec room, private heated pool, and private dock.

Guest favorite

Home in Seminole

4.88 out of 5 average rating, 141 reviews

Huge & Heated Pool Home 5 Minutes Away from Beach!

5⭐⭐⭐⭐⭐ Service & Accommodations This house is perfect for a relaxing vacation or a friend and family get-together. Perfect location 1 mile away from stunning Golf Coast beaches, including Madeira Beach, Indian Rocks, St Pete Beach, Clearwater Beach, and others. Features a heated pool all year long, billiards table, ping pong table and more! Please inquire about any questions whatsoever, and we will respond to you; we are available 24/7!

Guest favorite

Home in Seminole

5 out of 5 average rating, 112 reviews

WOW! Heated Pool and Hot Tub! NICE! 3 mi to beach!

No Damage from Milton and Helen! Are you ready for a stylish and perfectly renovated HUGE AMAZING HEATED POOL and HOT TUB home to escape to? Then look no further! Welcome to YOUR little slice of heaven- MASSIVE 13x 30 foot heated pool, NICE HOT TUB ! Updated home.Home is a super fast 5 min drive to the closest gulf beach. Nice fenced in yard. Pool heated oct15-april 15 at no extra fee! SUPER FAST WIFI 556mbpp