Holiday rentals in Sand Key

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Top-rated holiday rentals in Sand Key

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Top guest favourite
A modern living area showcases a comfortable blue futon and a wooden dining table with grey upholstered chairs. A flat-screen television is mounted on a wall featuring a contemporary design. Light flows from a nearby window, enhancing the inviting space.
Home in Largo
4.98 out of 5 average rating, 105 reviews

Newly Updated & Clean Vacation Home

Home is centrally located b/w Clearwater Beach 🏖️ , Dunedin 🌺, St. Petersburg 🍨 , and Tampa 🌃. Plenty of local restaurants & shops 🍒. Minutes from Indian Rocks Beach 🐚🏝️. 30-minute drive from Tarpon Springs Sponge Docks 🐬🐟. This super clean and fully stocked home offers everything you’ll need for an enjoyable stay. Home features a comfortable king bed and 1 futon sofa convertible bed, ideal for 1-3 guests. For added security, outdoor cameras operate 24/7. Please feel free to reach out!😊

Guest favourite
A bright living room features a gray couch with colorful accent pillows, positioned next to a coffee table. Large sliding glass doors open to a view of the patio. A rug with intricate designs lies on the floor, complemented by a cozy accent chair.
Apartment in Largo
4.9 out of 5 average rating, 224 reviews

Modern and Cozy Condo 6 Minutes from the Beach !

This condo is a true gem, conveniently situated only a 6 minute drive away from highly-rated Indian Rocks Beach, celebrated by TripAdvisor. You'll be pleased to know that there's a beautiful golf course just a few minutes drive. Situated on the first floor , this modern condo features a screened patio with views of serene fountain. The complex offers a pool, gas BBQ for grilling and free parking. Plus, it is ideally located near everything you need, including a Starbucks just a short drive away

Guest favourite
The exterior of a two-story condo is showcased, featuring a well-maintained entrance with a concrete pathway bordered by lush green grass. The building has multiple windows and a combination of beige and brown siding, along with a row of palm trees enhancing the tropical setting.
Flat in Oldsmar
4.91 out of 5 average rating, 22 reviews

Cozy Private 2BR FL condo

Experience ultimate relaxation in this perfectly located private home away from home. Relax on your enclosed lanai overlooking your wooded backdrop. Second floor condo with vaulted ceilings in pristine condition and complete with all furnishings & living essentials! Community Pool And close to Westfield Countryside Mall, area shopping, restaurants, public golf courses, entertainment, plus the sandy beaches of Honeymoon Island or Clearwater. located in the gated community-East Lake woodlands

Top guest favourite
An aerial view captures the serene coastline and vibrant community of Indian Rocks Beach. The expanse of blue water meets the sandy shore, with buildings and residences lined along the beach. Green parks and water channels are visible, enhancing the coastal atmosphere.
Flat in Indian Rocks Beach
4.96 out of 5 average rating, 120 reviews

Cozy coastal grandmother condo, walk to the beach!

Bright, stylish and quaint. Newly remodeled and furnished to make you feel like you're at your own beach home. Grab your provided beach chair and towel for your short jaunt down to the beach(a football field away) and take a deep breath; let the endless views, waves crashing and sand between your toes take you away. The well appointed kitchen can be used to simply make coffee or a full dinner. Don't feel like cooking? No problem! Indian Rocks Beach offers local coffee, lunch and dinner spots!

Top guest favourite
A private outdoor space features lush greenery framing a stone pathway leading to a wooden seating area. The area is adorned with tropical plants, creating a serene ambiance. A small bar-height table with stools is visible in the background.
Bungalow in Oldsmar
4.98 out of 5 average rating, 165 reviews

salt living at its best

- Resort Style Water front - Stand alone - Hot tub - Sunrise / sunset views on dock - free Kayaks - Internet / YouTube cable - 65” smart TV - Spacious Bedroom with king size bed, walk in closet and flat TV - Washer and Dryer in unit - Designated work space -Pet friendly - Fenced private patio - Free 2 cars / Boat Parking. - Central location ( beaches, restaurants, Tampa, St Pete’s, safety Harbor, Dunedin - 11 minutes from Ruth Eckerd event Hall - Pristine clean - Coffee station - Dining area

Top guest favourite
An open-plan living area displays a modern aesthetic, featuring a cozy sofa paired with circular wooden coffee tables. A blue accent wall contrasts with light cabinetry in the kitchen, where geometric light fixtures hang above the island. A large wall-mounted TV is positioned above a stylish sideboard.
Cottage in Indian Rocks Beach
4.98 out of 5 average rating, 192 reviews

Modern Coastal Hideaway –Patio & Hammock by Beach!

Sandy Toes Cottage is a fully renovated beach home just 2 minutes from Indian Rocks Beach. Enjoy modern furnishings, a bright kitchen, spa-style bath, free Wi-Fi, and a backyard with fire pit and hammock. Walk to local dining and shops—your perfect coastal getaway! **NEW AIRBNB PRICING UPDATE** Starting mid-October 2025, Airbnb will show all-in pricing—including an increase fee of 15.5% Airbnb service fee (charged directly by Airbnb to me the host), cleaning fees, and pet fees if applicable!

Top guest favourite
A tranquil waterfront view is captured during sunset, featuring a heated pool and spacious hot tub. Surrounding palm trees add a touch of greenery, while the Belleair Bridge is visible in the distance against a colorful sky reflected in the water.
Home in Indian Rocks Beach
5 out of 5 average rating, 27 reviews

New Waterfront house pool hot tub golf cart kayaks

BTR# 2367 Birds of Paradise is a stunning 3 bedroom 2 bathroom waterfront house with heated pool and hot tub, deep water dock, 6-seat golf cart, kayaks and paddle board that is located just off Party Island in Indian Rocks Beach. The house offers an expansive and gorgeous view of the Belleair Bridge and quick access by boat to the Gulf of Mexico, Caledesi and Honeymooni Islands. Guests can use kayaks and paddle board provided to spend an afternoon on Party Island, just off the house. 🌴🌊🌞

Guest favourite
Home in Indian Rocks Beach
4.89 out of 5 average rating, 152 reviews

Azule|Waterfront | Walk to Beach-Dock-Bikes-Kayaks

Welcome to Villa Azule, your luxurious Indian Rocks Beach retreat! - Spacious 2,646-square-foot waterfront haven with stunning canal views. - Two king master bedrooms and a queen bedroom, accommodating up to 10 guests. - Outdoor amenities include a boat lift, propane grill, fire pit, bikes, and kayaks. - Open concept living area perfect for relaxation and entertainment. - Close to local shops and a 10-minute walk to the beach. - Complimentary sparkling wine awaits your arrival.

Top guest favourite
A spacious bedroom is adorned with modern decor. A large bed with textured pillows is positioned across from two stylish chairs and small side tables. Natural light filters through three windows, creating a bright and airy atmosphere.
Flat in Dunedin
4.96 out of 5 average rating, 276 reviews

Private Balcony Apt Overlooking Dunedins Main St

This newly updated studio apartment is located in downtown Dunedin on Main Street. The large private balcony is the real gem. Inside you’ll find quality furnishings and attention to detail throughout. We are centrally located to both Tampa and St. Pete. Our award winning white sandy beaches are a short drive from the unit. Steps from your door you’ll find shopping breweries and dining options to please just about all. This unit is above a Pub/Bar, noise may be an issue.

Top guest favourite
Home in Indian Rocks Beach
5 out of 5 average rating, 100 reviews

Waterfront Duplex: 3 Blocks to Beach, Hot Tub, SUP

☀ Bay Views ☀ Shared Hot Tub ☀ Dock with Stand-up Paddle boards, Kayaks, Bikes ☀ Only 3 blocks to the sugary sands of Indian Rocks Beach ☀ Duplex- book independently or together ☀ Blackstone, 6 burner Charbroil Grill ☀ 10 Foot Custom Wood Bar w/ Jenga, Giant Connect 4, Corn Hole, Ringtoss ☀ Beach Wagons, Speaker, Zero Gravity beach chairs, beach towels, cooler ☀ Amazon Dot with Unlimited Amazon Music

Guest favourite
A bright living area features a comfortable light-colored sofa and armchairs, complemented by a decorative round coffee table. Large glass doors provide an unobstructed view of the beach and palm trees outside, allowing natural light to fill the space.
Apartment in Indian Rocks Beach
4.97 out of 5 average rating, 154 reviews

Private Ocean View Beach Retreat with Balcony

Only steps from the beach, this newly updated and perfectly located beach condo is your luxury getaway. The large bedroom, lofty living area and modern open kitchen, as well as the generous balcony with direct view of the Gulf will make you never want to leave again. This condo is better equipped than your average vacation rental and comes with your private daily sunset spectacle. Continue to read for more...

Guest favourite
A charming two-story building is nestled among lush greenery and vibrant flower beds. Large oak trees with hanging moss provide shade, while a welcoming staircase leads to the entrance. Outdoor seating areas are visible, enhancing the garden's tranquility.
Flat in Tarpon Springs
4.93 out of 5 average rating, 168 reviews

Cozy Carriage House at Spring Bayou

This is a beautiful large one bedroom apartment located in the heart of Tarpon Springs. The entire "2nd floor" apartment is yours to enjoy. Close to shopping, Greek village on the Anclote River , and many fine dining establishments. We are minutes from some of the most beautiful beaches in Florida. We are central to most of Florida's popular vacation attractions. You will love it.

Popular amenities for Sand Key holiday rentals

  1. Airbnb
  2. United States
  3. Florida
  4. Pinellas County
  5. Belleair Beach
  6. Sand Key