Vacation rentals in Sand Key

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Top-rated vacation rentals in Sand Key

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Top guest favorite

Home in Clearwater

4.98 out of 5 average rating, 177 reviews

Specious home W/ Heated Pool ! ! ! Great Location.

Cozy, spacious home 🏡 w/ heated swimming 🏊‍♀️ pool, next to a golf ⛳️ course. Close to the famous beaches ⛱️, St.Pete and Tampa. This cozy open home has a large living room, big kitchen and pool deck patio. All 3 bedrooms have large TV's w/ Sling & Roku. The big back patio has a swimming 🏊‍♀️ pool, TV, fridge and BBQ for cook outs & R&R. Located in a quiet family-friendly neighborhood. Location! 15 min - Clearwater Beach, Dunedin, Safety Harbor 30 min from - St.Pete, TPA Airport, Tampa

Top guest favorite

A large swimming pool is surrounded by lush palm trees and lounge chairs. The pool features a winding shape with a hot tub adjacent to it. Resort-style amenities are visible in the background, with a two-story building lined with windows overlooking the pool area.

Condo in Clearwater

4.97 out of 5 average rating, 130 reviews

2 BR/2 BA Retreat, Immaculate, 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 favorite

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

4.99 out of 5 average rating, 134 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 favorite

A view from the balcony captures a stunning sunset over the Gulf, where vibrant hues blend in the sky. The sandy beach is visible below, with a winding path leading to the shoreline. Figures can be seen strolling along the beach, adding life to the serene scene.

Apartment in Independence Square

4.96 out of 5 average rating, 170 reviews

Direct Ocean View Top Floor Renovated. 2BR, 2 Bath

The Marquise 204 is a Beautiful 1300sq ft DIRECT beachfront unit! Direct Gulf front views! Top floor corner unit. Small and quiet 10-unit building. Tremendous location for getaways with family and friends. After arriving you can literally leave your car behind and walk to over 10 local restaurants, bars and shops! Enjoy some of the best sunsets you will see in all of Florida from your private balcony! NO PETS. Renter MUST be at least 25 years old. NOTE: TWO flights of stairs NO elevator.

Guest favorite

A spacious living area is highlighted by a large sectional sofa and a glass dining table surrounded by white chairs. Natural light fills the room through expansive glass doors, offering views of the outside. Elegant light fixtures enhance the welcoming ambiance.

Condo in Sand Key

5 out of 5 average rating, 10 reviews

Magnificent Beachfront Condo on Sand Key

Welcome to your Beach Getaway! Please inquire if interested in less than a 14 day Stay. Enjoy your stay in our spacious condo in the Luxurious Crescent Beach Club on Sand Key. This condo offers over 2 Large Bedrooms, 2.5 Bathrooms, Full Kitchen, Large Living Area, Multiple Balconies! Soak up the sun by the pool, relax in the hot tub, get a workout in at the Fitness Center or just lay on the white sand beach. The Crescent Beach Club is the perfect vacation destination for your Family!

Top guest favorite

A sandy path leads through lush greenery towards the beach, framed by overhanging branches. The ocean is visible in the distance, with light reflecting off the water. Shadows create a peaceful atmosphere as the sun casts a warm glow.

Cottage in Indian Shores

4.96 out of 5 average rating, 169 reviews

Beautiful Beachfront Cottage on the Water

Renovated, romantic 1937 beach front cottage. Last of its kind in the quiet family setting of Indian Shores Florida, halfway between Clearwater Beach and Treasure Island/John's Pass. Truly an "Old Florida" experience with original pine floors, Florida room and covered porches, as well as updated kitchen and bathroom. This house, uniquely built near ground level, allows it to be waterfront on the beach while shaded by huge pine trees. You won't find a more tranquil setting on the beach.

Guest favorite

The bathroom features a clean, modern design with a white vanity and granite countertop. A round mirror is above a double sink, and a small window allows natural light. Bath towels are neatly arranged, and a decorative piece adds a subtle touch to the wall.

Guest suite in Largo

4.82 out of 5 average rating, 274 reviews

Cozy Largo Studio

Wonderful studio consisting of a comfortable queen bed, and small kitchenette, perfect for a long term stay or weekend get away. Parking on premises. Unit was newly renovated and is impeccably kept. This is a one room studio, minutes away from popular Indian Rocks beach / Belleair beach and clear water beach. Easy hassle free check in. (This is a one room studio with 1 queen bed as shown) this is a private apartment with its own front door. Medical students welcome!

Top guest favorite

An exterior view of a yellow condo building is depicted, featuring palm trees and shrubs. A pathway leads to a private entrance, while large windows allow ample natural light. The surrounding landscaping creates a welcoming atmosphere in the gated community.

Condo in Clearwater

4.95 out of 5 average rating, 125 reviews

Bright and Spacious 1Bed/1Bath condo.

Enjoy your getaway in this relaxing, clean, bright, and cozy 1 bedroom/1 bath condo on the 1st floor of a gated community, fully equipped for your stay including beach chairs, umbrella and a cooler. You will have a private entrance to the condo, free parking, a heated pool open all year, a clubhouse with a basic gym. We are conveniently located 15 minutes away from Clearwater Beach and an easy 30-minute drive to Tampa International Airport.

Top guest favorite

The grotto-style pool area features natural rock formations with cascading waterfalls and lush tropical plants. A hot tub is integrated into the design, providing a relaxing space. The serene water reflects the clear blue sky, while views of the bay are visible in the background.

Home in Oldsmar

5 out of 5 average rating, 144 reviews

Bayside Retreat your tropical oasis

"Bayside Retreat" is a Charming Private 1~bedroom/1 bath with full living room suite, located right on the water of upper Tampa Bay. Spend a quiet day lounging in the grotto pool, kayaking the bay, or a lazy day reading in the hammock. Enjoy breath taking sunrise and sunsets from the dock. Your own Tropical Paradise away from the rest of the world....... Just 15min to Raymond James Stadium. Centrally located 15 miles from TPA Airport

Guest favorite

A tranquil bedroom features a queen-sized bed with a patterned blue quilt and decorative pillows. Soft lighting from two bedside lamps enhances the calm ambiance. A ceiling fan is positioned above, and art pieces are displayed on the walls. A doorway leads to other areas of the apartment.

Apartment in Largo

4.84 out of 5 average rating, 269 reviews

Upper Old Oaks Bungalow 15 min to Clearwater Beach

NOTE: We lost two big trees in the backyard so the paving walkway is a little out of sorts & the train track in the back is visible. Please check post-hurricane photos of the backyard. We priced it accordingly. If any of these concern you, we encourage you to book elsewhere. Apartment is newly remodeled. New kitchen & bathroom w/ standing shower (no tub). New photos soon! You're renting half of a duplex. You will be staying upstairs.

Top guest favorite

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.

Condo in Clearwater

4.99 out of 5 average rating, 104 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!

Top guest favorite

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.

Condo in Indian Rocks Beach

4.97 out of 5 average rating, 145 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...