Photo by Travel Ginger

Holiday Homes in Keystone

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
15 Aug - 17 Aug
In two weeks
22 Aug - 24 Aug
In one month
5 Sept - 7 Sept
In two months
3 Oct - 5 Oct

Featured Holiday Homes in Keystone

Luxury waterfront townhome, 5 min to beach, pool, boat slip & rooftop deck!
Enjoy al fresco dining with a round table and six chairs, overlooking the city and a body of water.

Luxury waterfront townhome, 5 min to beach, pool, boat slip & rooftop deck!

10.0 out of 10, Exceptional, (69)
"We had so much fun at this beautiful home and wish we were still there!"
Luxury waterfront townhome, 5 min to beach, pool, boat slip & rooftop deck!
*Your Large 2nd Home in Tampa Bay* **Thoroughly Sanitized**
Enjoy cooking in this kitchen with a central island and bar stools, featuring appliances and a convenient coffee station.

*Your Large 2nd Home in Tampa Bay* **Thoroughly Sanitized**

9.8 out of 10, Exceptional, (68)
"The house is beautiful and the location was perfect for what we needed. "
*Your Large 2nd Home in Tampa Bay* **Thoroughly Sanitized**
Breezy ‘White Sands House’ Steps to Gulf Shore!
Enjoy cooking in this well-equipped kitchen with stainless steel appliances and a spacious tiled backsplash.

Breezy ‘White Sands House’ Steps to Gulf Shore!

9.6 out of 10, Exceptional, (103)
"Great access to the beach, parking on the property, and plenty of space to relax and hang out. "
Breezy ‘White Sands House’ Steps to Gulf Shore!
Centrally Located 3-Bedroom Oasis: 20 Mins to Beach and City Life on VRBO
Relax in this inviting living space with a large L-shaped sofa, coffee table, and patterned rug.

Centrally Located 3-Bedroom Oasis: 20 Mins to Beach and City Life on VRBO

7.0 out of 10, Good, (6)
"A beautiful house, very comfortable, it has a beautiful yard and the house is close to all the shops. "
Centrally Located 3-Bedroom Oasis: 20 Mins to Beach and City Life on VRBO
1 Bedroom Penthouse Suite located within the Sandpearl Resort & Spa
Relax in comfort on the beach with Adirondack chairs and enjoy a safe and well-maintained environment.

1 Bedroom Penthouse Suite located within the Sandpearl Resort & Spa

10.0 out of 10, Exceptional, (272)
"This property is amazing, and we would absolutely stay here again!"
1 Bedroom Penthouse Suite located within the Sandpearl Resort & Spa
Mod 4BR Home, Heated Private Pool • Near Indian Shores & John’s Pass • Sleeps 10
Guests can enjoy the serene beach scene with calm waters and a lifeguard tower nearby.

Mod 4BR Home, Heated Private Pool • Near Indian Shores & John’s Pass • Sleeps 10

9.8 out of 10, Exceptional, (23)
"This property was fantastic. Plenty of room and amenities for all. Kitchen had everything we needed to make some easy meals. Pool was clean and warm. The whole property was well maintained. Would definitely book here again. "
Mod 4BR Home, Heated Private Pool • Near Indian Shores & John’s Pass • Sleeps 10
La Casita Blanca Ybor City Tampa
Cozy retreat with a white door, small window, and kitchenette area.

La Casita Blanca Ybor City Tampa

9.8 out of 10, Exceptional, (106)
"We are definitely planning to stay here again"
The price is AU$236
includes taxes & fees
11 Aug - 12 Aug
La Casita Blanca Ybor City Tampa
*Pool* 8.5 miles to Honeymoon Island. 4 bdr
Enjoy the tranquil atmosphere of Clearwater Beach, where guests can soak up the sun and take in the breathtaking ocean views.

*Pool* 8.5 miles to Honeymoon Island. 4 bdr

10.0 out of 10, Exceptional, (42)
"Loved the area and comfortable accommodations. "
*Pool* 8.5 miles to Honeymoon Island. 4 bdr
Private Pinellas County Beaches' getaway house
Enjoy outdoor dining or relaxation in this serene patio area with a table and chairs, surrounded by a lush garden and a string of twinkling lights.

Private Pinellas County Beaches' getaway house

8.4 out of 10, Very good, (42)
"Comfortable, complete and perfect"
The price is AU$243
includes taxes & fees
10 Aug - 11 Aug
Private Pinellas County Beaches' getaway house
Charming Clean Studio in Downtown Clearwater
Simple, single-story building with a blue door and a chair outside, surrounded by palm trees and a gravel pathway.

Charming Clean Studio in Downtown Clearwater

9.6 out of 10, Exceptional, (14)
"Everything was as advertised. Great location for beach in clearwater and tampa."
The price is AU$211
includes taxes & fees
10 Aug - 11 Aug
Charming Clean Studio in Downtown Clearwater
Spacious Tampa Haven: Games / Pool / 7-15 min From Everything
Relax in this stylish living room with a sofa, flat-screen TV, and vibrant artwork.

Spacious Tampa Haven: Games / Pool / 7-15 min From Everything

9.2 out of 10, Wonderful, (12)
"Beautiful home, the Owner was very friendly and accommodating to our needs. Responded to emails in a timely manner. Next time I'm in Tampa I would love to stay here again."
Spacious Tampa Haven: Games / Pool / 7-15 min From Everything
House with unique style 3/2 Near Raymond Stadium
Enjoy cooking in this well-equipped kitchen with oven, microwave, and coffee maker.

House with unique style 3/2 Near Raymond Stadium

7.6 out of 10, Good, (63)
"Perfect for what we needed to attend NY Yankees spring training games. "
The price is AU$378
includes taxes & fees
20 Aug - 21 Aug
House with unique style 3/2 Near Raymond Stadium
5805 S Hubert Ave · Charming Tropical Pool Retreat w Hot Tub
Relax by the serene pool surrounded by lush greenery and trees.

5805 S Hubert Ave · Charming Tropical Pool Retreat w Hot Tub

9.2 out of 10, Wonderful, (47)
"We wanted to check out south Tampa and we’re happy with this location for our two week stay. Kids loved the pool and hot tub everyday! "
The price is AU$565
includes taxes & fees
14 Aug - 15 Aug
5805 S Hubert Ave · Charming Tropical Pool Retreat w Hot Tub
Clearwater Beach House - Right On The Beach
Enjoy a serene beach experience with calm seas and gentle waves.

Clearwater Beach House - Right On The Beach

9.6 out of 10, Exceptional, (112)
"Convenient to Beach and local restaurants"
The price is AU$780
includes taxes & fees
12 Aug - 13 Aug
Clearwater Beach House - Right On The Beach
Paradise Privacy Cottage
Relax on the patio with a wicker sofa, round table, and two chairs.

Paradise Privacy Cottage

9.0 out of 10, Wonderful, (20)
"This was perfect for my daughter and I, located in a cute neighborhood and close to many things. It was very clean and allowed for privacy, definitely felt like home away from home and would highly recommend. "
The price is AU$222
includes taxes & fees
10 Aug - 11 Aug
Paradise Privacy Cottage
Delightful and Quaint 3BR/2BA Ybor Bungalow
Enjoy a view of lush greenery from the kitchen window, where you can cook and relax.

Delightful and Quaint 3BR/2BA Ybor Bungalow

9.0 out of 10, Wonderful, (54)
"Great stay, perfect location!!! We love Ybor!!"
The price is AU$387
includes taxes & fees
12 Aug - 13 Aug
Delightful and Quaint 3BR/2BA Ybor Bungalow
Endless Summer Pool Vibes
Relax by the pool surrounded by lush greenery and an outdoor space.

Endless Summer Pool Vibes

9.2 out of 10, Wonderful, (22)
"Comfortable beds, convenient location, clean, "
Endless Summer Pool Vibes
New Luxury House Pool. Just 14 Minutes From the Airport
Enjoy a warm and inviting living space with a fireplace, comfortable seating, and a central kitchen island.

New Luxury House Pool. Just 14 Minutes From the Airport

9.4 out of 10, Exceptional, (19)
"Recommended place in Tampa"
New Luxury House Pool. Just 14 Minutes From the Airport
Private Oasis Retreat Heated Pool Hot Tub Beaches
Relax in the hot tub surrounded by comfortable seating and a view of the adjacent pool.

Private Oasis Retreat Heated Pool Hot Tub Beaches

10.0 out of 10, Exceptional, (18)
"We enjoyed this place very much. We spent a lot of time around the pool very nice area."
Private Oasis Retreat Heated Pool Hot Tub Beaches
Modern 3bed, 2bath House in Wesley Chapel, with EV Charging Outlet, AC, & WiFi.
Enjoy cooking in this well-lit kitchen with a central island and stainless steel appliances.

Modern 3bed, 2bath House in Wesley Chapel, with EV Charging Outlet, AC, & WiFi.

9.6 out of 10, Exceptional, (10)
"Property was clean and owners responsive to all needs. Check in was easy. Not sure if dogs are allowed but if so yard was dog friendly. "
Modern 3bed, 2bath House in Wesley Chapel, with EV Charging Outlet, AC, & WiFi.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free