Holiday rentals with a pool in Sand Key

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Top-rated rentals with a pool in Sand Key

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

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A spacious pool area features a large, inviting swimming pool surrounded by lounge chairs and palm trees. The pool is designed with a gradual slope, leading to a hot tub section. The well-maintained landscape adds to the relaxed atmosphere of the community.
Apartment in Clearwater
4.74 out of 5 average rating, 111 reviews

Beautiful Cozy Condo 3 miles away Clearwater Beach

AVALON CONDO This gated community is located 3 miles away from Clearwater Beach (voted #1 beach in the US Tripadvisor) ONE BEDROOM ONE BATH WALK IN SHOWER GRANITE KITCHEN ISLAND WITH SEATING FOR 3 GROUND FLOOR ( dont carry your luggages or beach supplies up the stairs) KING SIZE BED 1 SMART TV, INTERNET ACCESS, NETFLIX 2 FLAT SCREEN TV 50 INCHES FULL SIZE WASHER AND DRYER BEACH SUPPLIES ( UMBRELLA, CHAIRS, COOLER, BEACH TOWELS) SLEEPING SOFA STEPS AWAY POOL FREE PARKING TRAVEL NURSE WELCOME

Guest favourite
Apartment in Clearwater
4.97 out of 5 average rating, 131 reviews

2 BR/2 BA Key West Retreat, A+Pool, 3m 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.

Top guest favourite
The bedroom features a spacious bed adorned with patterned pillows, complemented by two bedside tables with decorative lamps. Artistic wall frames in muted tones enhance the ambiance. A soft glow is provided by lighting, and sheer curtains allow natural light to filter in.
Apartment in Clearwater
4.98 out of 5 average rating, 140 reviews

Modern condo, minutes to the beach, free parking

This amazing condo is a 5-minute drive to the beautiful Clearwater Beach,as well as bars, restaurants, and many other attractions. The unit is placed in a beautiful resort-style gated community, which features a clubhouse, heated pool, gym, Wi-Fi, and complimentary parking. This perfect retreat offers full privacy as each room provides separate access to the bathroom. The condo is on the main floor, offering easy access in and out, and includes a laptop-friendly workspace. Just come and relax!

Top guest favourite
A clear blue pool is surrounded by lush greenery, including palms and other tropical plants. A red umbrella provides shade over a seating area nearby, while lounge chairs are positioned along the pool's edge, inviting relaxation in a serene outdoor setting.
Guest suite in Largo
4.97 out of 5 average rating, 386 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.

Top guest favourite
An inviting heated saltwater pool is softly lit in the evening, surrounded by sun loungers. The vibrant mural features a large tropical flower. A close-up shows a decorative pillow with the word 'SUNSET.' The living area offers a cozy seating arrangement with colorful cushions and a decorative coffee table.
Cottage in Indian Rocks Beach
4.96 out of 5 average rating, 161 reviews

Luxury Beach Bungalow | Walk to Dining & Sunset

Escape to paradise at Sunshine Escapes! Welcome to #MangoIRB, nestled in the heart of Indian Rocks Beach. IRB is a hidden gem radiating a whimsical, small-town charm that evokes nostalgic memories of carefree childhood summers by the shore. Just ✌🏽 blocks away, the Gulf of Mexico beckons, offering pristine fluffy sand and unforgettable sunsets. As the sister cottage of Coco, #MangoIRB invites you to immerse yourself in the laid-back beachy vibes of IRB. Your perfect beach getaway awaits!

Top guest favourite
A spacious living area features a gray sectional sofa and two patterned armchairs. A large wall clock and artwork with the word 'RELAX' are displayed. Natural light enters through sheer curtains, while a sliding door provides access to the private patio. A coffee table with decorative items is in the center.
Apartment in Clearwater
4.86 out of 5 average rating, 109 reviews

Clearwater Condo w/Pool Access, 4Mi to Beach!

Clearwater Condo w/Pool Access, 4Mi to Beach! The crystal-blue Gulf Coast is calling from this charming 1-bedroom, 1-bath vacation rental condo just minutes from downtown Clearwater! Spend your days exploring downtown Clearwater or St. Petersburg, or enjoying the heated community pool. This single-story condo comfortably sleeps 2 and boasts tall ceilings, a fully equipped kitchen, private patio, and access to all of the Avalon's community amenities, including a pool, gym, clubhouse & more

Guest favourite
An open-concept living area features a full bed, a cozy couch, and a Smart TV mounted on the wall. Natural light enters through two windows, complemented by green walls and soft curtains. A dining table with colorful chairs adds a welcoming touch to the space.
Flat in Clearwater Beach
4.84 out of 5 average rating, 106 reviews

Renovated 2025 - Retro Beach Oasis with Color Pop

Book with confidence—our property is in great shape and ready to host your Clearwater Beach getaway! -No hidden fees -No chores Just a breezy, beachy stay with: -2-minute walk to the beach -Beach Chairs -Free parking -Heated pool -Cold AC -Easy self check-in -Pet friendly (One Pet max -$150 fee) We provide essentials (linens, towels, toilet paper, soap etc.) to get you started. For longer stays, we recommend buying additional supplies. 📍648 Poinsettia Ave, Clearwater Beach, FL 33767

Top guest favourite
The inviting pool area is surrounded by palm trees and features a vibrant pink flamingo float. Comfortable chaise loungers line the pool deck, offering relaxation options. A wooden fence provides privacy, and the outdoor space is designed for leisure and enjoyment.
Flat in Indian Rocks Beach
4.95 out of 5 average rating, 129 reviews

Triplex across from the beach, heated pool, bikes

☀ Easy access to the beach; just walk across the street! ☀ Stylish shared pool with sunshelf and chaise loungers ☀ Triplex with 3 uniquely decorated suites- private interiors, shared exterior ☀ Fire pit with relaxing swivel lounge chairs, bikes ☀ Beach wagons, zero gravity chairs, cooler, ice, umbrellas, towels, speakers ☀ 3 hole glow in the dark putt putt ☀ Amazon Dots with Unlimited Amazon Music ☀ Fenced-in courtyard w/ outdoor seating, umbrellas, and BBQ grills

Guest favourite
A modern kitchen is showcased with stainless steel appliances and a central island featuring bar seating. Sleek cabinetry and a bright light fixture enhance the space. Natural light fills the room, emphasizing the clean lines and functional design.
Apartment in Clearwater
4.97 out of 5 average rating, 111 reviews

Cozy Retreat, private unit, NO PETS

The Avalon at Clearwater is a gated community with a nice size heated pool and community gym. Parking space is not assigned and it’s free of charge. Walk-in distance to Publix grocery store and nearby restaurants. Location is central with short distance to nearby beaches, attractions and other nearby towns. Great access from Tampa Airport 20 minutes and 1.5/hours drive from Orlando airport and Disney World This location is loved by “snowbirds”

Top guest favourite
A spacious pool area features a large, inviting blue pool surrounded by lounge chairs and palm trees. A hot tub is situated near the pool, with umbrellas providing shade. The buildings of the gated community are visible in the background.
Apartment in Clearwater
4.99 out of 5 average rating, 107 reviews

Literally: 15 steps to the Pool, GroundFloor Condo

Unwind at this stunning Complex at Clearwater that resemble a vacation resort, gated community, extremely safe. Don't want to go out? There is everything you need right in the complex: Free Parking, 24/7 Free Gym, steps to the heated Pool with BBQ area and other wonderful-friendly guests for company (if needed), shops and few dining places in walking distance, your private patio to sit, drink, chat and relax; take some time for you!

Guest favourite
The exterior of a two-story condo building is featured, surrounded by tropical palm trees and well-maintained greenery. A paved walkway winds through the landscape, leading to the entrance of the building. The facade includes large windows, allowing natural light to fill the interiors.
Apartment in Clearwater
4.87 out of 5 average rating, 126 reviews

Cozy 1 bedroom condo.

Enjoy Clearwater from this beautiful 700 SFT, 1 bedroom condo with year-round access to a heated pool and only a 15 minute drive from Clearwater Beach. 2nd story condo with a single flight of stairs not shared by any other apartments. Safe and quiet gated community. Gym next to the pool. Parking is unassigned with plenty of spots next to the buildings. Beach chairs, umbrella, towels, cooler and other items available for your use.

Guest favourite
A bright studio space features a cozy seating area with a soft blue love seat and a spacious bed adorned with white linens. Natural light filters through sheer curtains, illuminating the wood furnishings and decorative accents throughout the room.
Guest suite in Largo
4.91 out of 5 average rating, 322 reviews

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

Welcome to our cozy guest suite—where comfort is personal over perfect, and full of charm you won’t find at a hotel. Guests love the thoughtful touches, eclectic decor, cloud-like bed, and the irreplaceable feeling of being at home when you’re far from home.

Popular amenities for Sand Key rentals with a pool

Quick stats about holiday rentals with a pool in Sand Key

  • Total holiday rentals

    Explore 130 holiday rentals in Sand Key

  • Nightly prices starting at

    Sand Key holiday rentals start at £37 per night before taxes and fees

  • Verified guest reviews

    Over 500 verified reviews to help you choose

  • Family-friendly holiday rentals

    90 properties offer extra space & child-friendly amenities

  • Rentals with dedicated workspaces

    80 properties have a dedicated workspace

  • Wifi availability

    130 of Sand Key holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Sand Key rentals

  • 4.8 Average rating

    Sand Key stays are highly rated by guests – averaging 4.8 out of 5!

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