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Vacation rentals with a pool in Sand Key, Clearwater

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Sand Key, Clearwater

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

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Home in Clearwater Beach

4.97 out of 5 average rating, 206 reviews

Clearwater Beach Townhome w/Game Room & Boat Slip!

PLEASE ASK ABOUT OUR OTHER 2 WATERFRONT PROPERTIES ON CLEARWATER BEACH IF YOUR DATES ARE NOT AVIALABLE!! Welcome to Brightwater Blue, our newer vacation Town Home in Clearwater Beach! 3 floors of fun, elegance & relaxation await you. Custom interior decorated with Restoration Hardware & other high end furnishings. Located on Clearwater Bay & within easy walking distance to Clearwater Beach, Beach Walk, restaurants, shopping & everything Clearwater Beach has to offer! Why book 3 hotel rooms when

Condo in Clearwater

4.98 out of 5 average rating, 113 reviews

Key West Retreat, 2 Bdrm, A+ Pool, 2.9 mi to Beach

🌴 😎 Stunning Key West Style Retreat featuring: - Memory foam Queen bed - Covered porch for unwinding - Hotel linens, towels and many creature comforts Enjoy the beach 🏄‍♂️ vibes decor & accents in this spacious two bed two bath property. Located less than three miles from the white, sugar sand of Clearwater Beach 😎 (rated #1 beach in the US by Trip Advisor). Relax by the oversized resort style pool and clubhouse. Convenient walking distance to nearby restaurants and grocery stores.

Rental unit in Clearwater

4.99 out of 5 average rating, 390 reviews

Private studio attached to house. Pool&bikes

Completely private A/C studio, bathroom & your own private saltwater pool. Studio attached to house. No cleaning fee. 1 block W to Edgewater trail. Beautiful sunsets on water. 1 block E to famous Pinellas trail. Stroll to downtown Dunedin or TD Stadium. Cruiser bikes provided. Drive, Uber, trolley or bike 4.5 miles to Clearwater Beach or Honeymoon Island. Near restaurants, shops, dancing, kayaking, fishing, boating, biking, baseball, etc! Space is not appropriate for under 18, pets, parties.

Home in Indian Rocks Beach

4.84 out of 5 average rating, 325 reviews

Stunning views! Spot dolphins from the pool!

BTR#2114 This home has it ALL including incredible open water sunsets! Every detail has been carefully thought out and updated. This is a VERY upscale, coastal, single story waterfront home. A complete waterfront remodel w/ dock & pool that looks and feels like a new home w/ stunning water views from your own back patio! The water glistens and sparkles from 3 pm thru sunset and after, the sky is set on fire for 40 minutes. White sandy beach is only few blocks away! Amazing home inside & out!

Condo in Clearwater Beach

4.98 out of 5 average rating, 126 reviews

Upgraded 3 Bed, 3 Bath Corner Water Front Condo!

Stylish & Sunny Corner Unit On Dolphin Faved Inlet Across The Street From Florida's #1 Beach. This all-inclusive unit allows you to walk everywhere and enjoy all Clearwater Beach has to offer from sand & sun to restaurants & shopping. Updated & upgraded 3 bedroom, all with connected bathrooms offers amazing space, a chef's kitchen as well as bright & beautiful dining & living rooms. Private balcony to relax & watch the sunset. Beach concessions include sea kayaks, jet ski's, boating & more.

Guest suite in Largo

4.93 out of 5 average rating, 268 reviews

"Twilight Sands Stud" Prvt Ent,Pool,Pk,Keyless Ent

Welcome to your private Studio located 10 minutes from Indian Rocks Beach FL. Come stay with us and dip your toes in the warm white sugar sands of the Gulf of Mexico. Our beautiful cozy studio has private parking, entrance and keyless entry, cozy cal king bed, on suite bath/shower w/bidet, sweet retro kitchenette including mini fridge/freezer, microwave and Keurig coffee/tea express. Beat the crowd, book your stay, relax at the best beaches in the country or explore Tampa Bay or St.Pete!

Townhouse in Clearwater Beach

5 out of 5 average rating, 108 reviews

Waterfront Beach House Steps Away from #1 Beach!

Welcome to The Bombshell Beach House! This 3 story, 3 bedroom luxury water-front townhouse located in Clearwater Beach, FL has been a childhood dream come true for me as a Clearwater native! As avid travelers, my husband and I wanted to create a STAY-CATION spot that mixed in all of the comforts of HOME with all of the luxuries of a 5 star vacation & this beach house is JUST THAT! This listing is brand new and we are expecting dates to book extremely fast! Book now to secure your GETAWAY!

Guest suite in Largo

4.97 out of 5 average rating, 341 reviews

Private Pool, Jacuzzi, Walk to Beach.

This Guest Suite is a large Studio Apt(360 sq ft) attached to our home. It has a private entrance, a large bath, large bedroom with pool view and private deck. Also includes a kitchenette with full size fridge, toaster, coffee maker and microwave. No Stove. Complimentary breakfast snacks including Coffee, tea and biscuits. Relax on the deck and watch the birds on the bird feeder or grab our bikes, beach chairs and head to the beach. Grill available. Please read house rules before booking.

Condo in Clearwater Beach

4.9 out of 5 average rating, 301 reviews

Amazing views on beachfront

This spacious upper-floor, 3-bedroom condo hotel suite offers views of the Gulf of Mexico from your private balconies. While preparing your morning coffee on the spacious kitchen island, you can see the water of the Gulf of Mexico. Each suite can accommodate 10 people, with 3 bedrooms, 2 of them with a King bed in each bedroom and the third with 2 Queen beds, each of them with their own ensuite bathroom, in total 3 1/2 bathrooms, also a comfortable full-sized sofa bed in the living room.

Home in Indian Rocks Beach

4.98 out of 5 average rating, 119 reviews

Beachfront Bungalow w/ Pool & Hot Tub in IRB

Beach front house with a saltwater pool! This 2 bedroom, two bath house is equipped with a newly renovated kitchen and new appliances. You will have your own private beach access with 2 outdoor showers. The outdoor dining area is perfect for dinner under the sunset. We are stocked with beach chairs, umbrellas, pool/beach toys, & floats. Close to parks, restaurants, & across the street from a small grocery store. Perfect for families or couples looking for a getaway in the sunshine state.

Rental unit in Clearwater Beach

4.86 out of 5 average rating, 199 reviews

Surf n Sand Studio Apartment by the Water 14

We were hit by 2 powerful hurricanes in the past month. As of now we are estimating to fully re-open on December 20th. In the meantime our upstairs rooms will stay open for guests who need a place to stay. Our rooms upstairs haven’t been damaged however we will not have wifi until November 20th and the pool will open on November 10th. Also, we will be working on fixing the rooms downstairs. Thank you for your understanding, and we really appreciate all the kind massages during this time.

Condo in Clearwater

4.89 out of 5 average rating, 188 reviews

Very cozy quality condo close to Clearwater Beach

Modern and very cozy one-bedroom condo, clean, quiet, and comfortable. Convenient big kitchen space and bathroom. King bed in master. Sleeping sofa in the living room. All appliances, kitchen pots, and all you need to make yourself home. TV in the living room and Master. Full cable. Fast WiFi. Roku. Beach towels, umbrella, chairs, cooler. 10 min from Clearwater Beach. 20 min from the airport. I put a lot of <3 INTO! You will feel at home in my place!:)

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Popular amenities for Sand Key, Clearwater rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

Home in Largo

4.86 out of 5 average rating, 108 reviews

The Paradise Cove No. 2

Home in Largo

4.94 out of 5 average rating, 101 reviews

Stylish Home. Heated Pool & Spacious Parking

Home in Clearwater

4.93 out of 5 average rating, 128 reviews

Modern Saltwater Pool Home Near Clearwater Beach!

Home in Clearwater

4.83 out of 5 average rating, 106 reviews

Heated Pool | 2BD 2BA | Home near Beaches

Home in Largo

4.95 out of 5 average rating, 128 reviews

Heated Pool Tropical Home 6min drive to the Beach

Home in Largo

4.92 out of 5 average rating, 65 reviews

Belleair Beach Oasis w/ Heated Pool - 3mi to Beach

Home in Clearwater

4.95 out of 5 average rating, 213 reviews

Heated pool, 12+ guests, large yard/pool

Home in Clearwater

4.86 out of 5 average rating, 107 reviews

Hot Tub, Heated Pool, Minutes to Clearwater Beach

Condo rentals with a pool

Condo in Clearwater Beach

4.99 out of 5 average rating, 127 reviews

Newly Reno Luxury Condo 30 Steps to Paradise

Condo in Clearwater

4.87 out of 5 average rating, 103 reviews

Amazing main floor condo at Avalon

Condo in Clearwater Beach

4.99 out of 5 average rating, 119 reviews

✔Waterfront |3BR |2Kings |Pool |Balcony |Beach

Condo in Largo

4.89 out of 5 average rating, 198 reviews

Modern and Cozy Condo 6 Minutes from the Beach !

Condo in Indian Shores

4.99 out of 5 average rating, 108 reviews

Tropical Beachfront Penthouse-Beach Cottages II

Condo in Clearwater

4.94 out of 5 average rating, 134 reviews

The Avalon - 1/1 LUXE CORNER CONDO/King size bed/

Condo in Clearwater

4.95 out of 5 average rating, 112 reviews

POOL VIEW IN A MODERN CONDO - Feel at Home

Condo in Clearwater

4.93 out of 5 average rating, 140 reviews

5 *Waterfront Condo,3 Beds,2 Baths, Pool, HOT-TUB.

Quick stats about vacation rentals with a pool in Sand Key, Clearwater

Total rentals
110 properties
Nightly prices starting at
$50 before taxes and fees
Total number of reviews
410 reviews
Family-friendly rentals
80 properties are a good fit for families
Rentals with dedicated workspaces
60 properties have a dedicated workspace
Wifi availability
110 properties include access to wifi

Destinations to explore