Sand Key, Clearwater vacation rentals

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Top-rated vacation rentals in Sand Key, Clearwater

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Guest favorite

Apartment in Indian Rocks Beach

4.93 out of 5 average rating, 117 reviews

Vintage Florida Beach Efficiency

Just a short walk to the beach, this a great beach getaway for couples or families with one child. On your way stop at the Cooky Coconut for lunch, an awesome milkshake or a variety of snacks. With a totally new renovation in 2022, this unit is updated, very clean & worry free. This cottage is located in a quiet residential neighborhood and a great place to relax. Laundry on shared screened porch. Dogs allowed ($35 extra) add them on # of guests page . Easy refund policy. Level 2 EV charger

Oct 20 – 27

$73 per night

Guest favorite

Apartment in Clearwater

4.95 out of 5 average rating, 154 reviews

Private Apt, Beach 2 mi, Walk to Park & Downtown

Beautifully remodeled 1930s apartment in a small building. Situated in a gorgeous, historic, walkable neighborhood. Only two short miles to Clearwater Beach. Walk or jog throughout the neighborhood, to Coachman Park, downtown, or over the bridge leading to Clearwater Beach. Two bicycles are usually available for guests. We are in close proximity to restaurants & cafes. Many of our guests attend concerts at The Sound at Coachman Park and shows at the Capitol Theatre. Animals are not permitted

Aug 24 – 31

$100 per night

Guest favorite

Apartment in Clearwater

4.99 out of 5 average rating, 352 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.

Jan 4 – 11

$130 per night

Guest favorite

Guest suite in Dunedin

4.94 out of 5 average rating, 202 reviews

Downtown Coastal Studio

Our Downtown Coastal Studio was recently renovated. The studio has a bright and airy atmosphere. Both clean and cozy, it is the perfect place to rest and relax. Located in the heart of downtown Dunedin and two blocks to the Pinellas Trail. Simply park your car and enjoy downtown on foot or rent a bike and cruise around. We are close to two major beaches, the marina, and John G. Hubbard Park, which is just across the street with a nice path to stroll along the water or take in the sunset.

Sep 23 – 30

$85 per night

Guest favorite

Guest suite in Largo

4.95 out of 5 average rating, 233 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!

Feb 23 – Mar 2

$80 per night

Guest favorite

Home in Clearwater

4.9 out of 5 average rating, 116 reviews

Coastal Cottage B - Bikes Beach Items

This lovely 2 bedroom 1 bath home is clean and modern! This home is a duplex but has no access between units -it was triple insulated on all walls. All bedrooms have brand new foam mattresses and new cold air/mini splits. This unit has many stairs-please see pictures. Access to the bathroom is through the downstairs bedroom. I just installed privacy curtains in both bedrooms (no actual bedroom solid doors. Sorry no animals/pets. Close to Dunedin, Honeymoon Island, and Clearwater beach! ❤️

Sep 8 – 15

$99 per night

Guest favorite

Condo in Indian Rocks Beach

4.79 out of 5 average rating, 225 reviews

Waterfront Condo w/ Boat dock, 2 min walk to beach

This cozy one bedroom, one bath condo is only 2 blocks from the beach with family-friendly activities, nightlife, and public transportation nearby. The place is perfect for solo travelers, couples, & even small families who looking to have a relaxing time. Located right on the intercostal waterway. You can enjoy your coffee on the dock while watching the sunrise. Also, a great spot for seeing dolphins. Shops, food , and entertainment are all located within walking distance. BTR #266

Aug 13 – 20

$99 per night

Guest favorite

Cottage in Indian Rocks Beach

4.93 out of 5 average rating, 176 reviews

Kooky Coconut Cottage, Indian Rocks Beach

Coconut Cottage only steps away from the beautiful beaches of Indian Rocks Beach. 2 bedroom,1 bath. The entire cottage has been renovated. Next door to the local famous Kooky Coconut Cafe. Perfect for couple, friends or small families. ONLY 3 GUESTS ALLOWED. NO sleeping on the sofa ALLOWED. If you bring more then 3 guests you will be charged $100.00 surcharge per night per extra guest. Due to cleaning restriction we DO NOT allow cooking with CURRY or FISH OIL in the cottage.

Jan 21 – 28

$155 per night

Superhost

Condo in Clearwater

4.83 out of 5 average rating, 119 reviews

Cozy Getaway close to Clearwater Beach

Modern and cozy one-bedroom condo 10 min away from gorgeous Clearwater Beach. It’s comfortable, high-quality, a quiet corner of the community, very clean. It has nice and comfortable furniture, fine sheets, blankets, towels, etc. Spacious fully equipped kitchen and big shower, king-size bed, sleeping sofa & relaxing patio. Beach towels, chairs, umbrella, cooler. TVs in the living room and bedroom, Full cable, ROKU. Heated pool, gated community, 24h gym. You’ll enjoy!!

Nov 4 – 11

$102 per night

Guest favorite

Home in Clearwater

4.93 out of 5 average rating, 101 reviews

NEW! renovated duplex minutes from the Beach!

Welcome to the beautiful city of Clearwater, and to our newly renovated duplex home. Conveniently located within 0.5 miles or 7 minutes walking to clearwater downtown, and 3 miles or 7 minutes driving to the famous and award winning Clearwater beach. Easy access to local restaurants, bars, stores, and parks. This comfortable home features an open layout with modern decor, free WiFi, smart Roku TV, tile flooring and sleeps up to 6 people. It also offers free parking .

Sep 26 – Oct 3

$106 per night

Guest favorite

Guesthouse in Clearwater

4.9 out of 5 average rating, 181 reviews

Cottage on Pinellas Bike Trail

This cottage on the trail is a gem. It is an easy one mile bicycle ride to downtown Dunedin and a quick stroll to waterfront Edgewater Park to watch sunsets or see the lights of Clearwater Beach across the intracoastal waterway. Circular driveway with a carport for off street parking. The cottage is equipped with a Keurig, microwave, mini fridge, as well as beach amenities and wifi. There's a fenced back patio for you to enjoy our beautiful weather!

Nov 11 – 18

$91 per night

Guest favorite

Home in Largo

4.91 out of 5 average rating, 348 reviews

Live Oak Lodge

Enjoy your stay in this 1950s tropical home in a quiet neighborhood only 3 miles from the beach. Two premium beach chairs, rolling cooler, umbrella and more to use during your stay! Hang out surrounded by the tropical plant life in the backyard. Cozy string lights drape the 6 foot privacy fence in the backyard. This is part of a duplex unit (another unit is attached to this one), but everything is private inside and outside. (No pets allowed :-))

May 21 – 28

$105 per night