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Holiday Rentals

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595 Results

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Price: low to high

Price: high to low

Number of reviews

595 Houses

Price per night from

$201

2 Bedroom waterfront vacation retreat

Holiday house

2 bedrooms / 2 bathrooms / sleeps 7

Responds fast! avg. 37 minutes

Price per night from

$172

Geodesic Dome

Holiday apartment

1 bedroom / 1 bathroom / sleeps 4

“Will and already have recomend to others.” Lots of fun places to see and eat at nearby. Sharon and Ralph made sure we had everything we needed.

Price per night from

$229

Dolphin Cove Villa

Holiday house

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$722

Snowbirds' Dream, Minutes from the Beach, Shopping, Nature and Biking Trails

Holiday house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 10 minutes

Price per night from

$194

Great rentals within 20 miles that match your search

Banana Breeze/Lazy Lemon Cottage-2 heated Pools, Clearwater Beach,Gulf of Mexico

Clearwater cottage

2 bedrooms / 1 bathroom / sleeps 5

Responds fast! avg. 1 hour 45 minutes

Price per night from

$131

The Cobbles

Hudson villa

3 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 2 hours 18 minutes

Price per night from

$166

Surfside Condos 204 Beachfront Condo

Clearwater apartment

3 bedrooms / 2 bathrooms / sleeps 10

“Surfsude Condo 204” The view was great....the condo was roomy enough for our family. Everything was good except needed more instruction on using TV in living room. Also needed more electrical outlets. We would stay here again. Had a great time.

Price per night from

$738

Bay Breeze House Waterfront home with pool

Clearwater house

4 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$291

*NEW* Spa Retreat: Relaxing Pool Home w/Hot Tub, Amenities and Conveniences

Tampa house

4 bedrooms / 3 bathrooms / sleeps 6

“Amazing Stay! Abolutely Loved This House!” My friends and I travel every year following our favorite football team and often look for homes to rent that provide many of the amenities you might find in high end hotels. In this home we found a gem. Property is amazing...well kept, spacious and convenient. Working with Paul was awesome and very welcoming. During the stay, Paul was always available at a moments notice if you needed anything. The home provided plenty of room for our group and the pool and spa are an extra added bonus. We were convenient to the highway, grocery stores and even Wal-Mart and restaurants. I will certainly look forward to staying in this property again when my travels bring me back to Tampa! Hats off to Paul and his team. Amazing Property!

Price per night from

$287

Desirable Resort Style Condo in Clearwater

Clearwater apartment

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$86

Clearwater Beach Waterfront #19. 2 Queen beds! Walk to all the fun!

Clearwater apartment

/ 1 bathroom / sleeps 4

“Cozy” Great condo. Close to the beach. Very clean. Has everything you could possibly need for the perfect Clearwater Beach vacation.

Responds fast! avg. 55 minutes

Price per night from

$144

Tampa TreeHouse

Tampa house

3 bedrooms / 3 bathrooms / sleeps 10

“Perfect Vacation Home!” This is the perfect vacation rental!! Clean, comfortable and well furnished. Close to beaches, entertainment and dining. The owner has all the bases covered and goes the extra mile to help with anything you need. I highly recommend this property for your vaction and am already planning our 2015 stay! Thanks again Javier!

Responds fast! avg. 3 hours 53 minutes

Price per night from

$423

Waterfront Home away from Home

Dunedin apartment

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 51 minutes

Price per night from

$115

Unforgetable Waterfront Cottage Retreat

Hudson cottage

2 bedrooms / 2 bathrooms / sleeps 7

“Great place to stay!” I often stay in vacation rentals for family visits, and this place in Hudson Florida was perfect. Pet birds on the fantastic dock; awesome TV; washer and dryer! When they say it has everything -- they mean it!! Thank you!

Responds fast! avg. 37 minutes

Price per night from

$172

Cozy carriage apartment in Tarpon Springs

Tarpon Springs apartment

1 bedroom / 1 bathroom / sleeps 4

“Great stay in Tarpon Springs” What a gem of a place. We had two bedrooms, full kitchen, living area and sun deck. What more could you want! gulf beaches, restaurants etc are all nearby. Super clean with all the necessary amenities including beach chairs, towels etc. The neighborhood is super quiet with lots of old Florida charm. It was three of us traveling including a friend and my husband. We felt right at home! Would highly recommend this place.

Responds fast! avg. 3 hours 44 minutes

Price per night from

$149

Comfy Cozy Cul de Sac Home in Beacon Woods East

Hudson house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 3 minutes

Price per night from

$115

Clearwater Beach Furnished Condo

Clearwater apartment

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$163

Exclusive Tropical Retreat in Sunny Clearwater Bea

Clearwater house

4 bedrooms / 4 bathrooms / sleeps 12

Price per night from

$480

SUNNY ALL DAY modern condo near Gulf of Mexico beaches

Clearwater apartment

1 bedroom / 1 bathroom / sleeps 2

“CLEARWATER'S BEST KEPT SECRET” The pictures sold me on this condo. It is exactly as it shows. Very clean, smells good. Great locations, all stores close on the same road as condo. Close to the beach. Owner kept in close contact throughout our pre-booking and stay. I will stay here again! Very, very nice.

Responds fast! avg. 2 hours 15 minutes

Price per night from

$172

Cove Cay Condo

Clearwater apartment

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 1 hour 16 minutes

Price per night from

$54

beautiful condo with magnificent views of mandalay

Clearwater apartment

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$153

Wonderful Belleair Beach Condo

Belleair Beach apartment

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$98

Clearwater Beach Hideaway Cottage, 3 bedrooms, Pets OK, Steps to the sand.

Clearwater cottage

3 bedrooms / 1 bathroom / sleeps 10

“Best weekend to the end of the summer” The hideawy cottage was perfect for what we needed peacefully, quite and dog friendly that what was the best part! The staff was great and professional and helpful. This was a perfect getaway for my birhtday celebration. I am turly coming back to take another mini vacation it was all the comfronts of home. I would like to thank the staff at Blue Wave Condo Suites for a wonderfully experience and this will be my new vacation spot when I travel back to Clearwater Beach.

Price per night from

$411

Dunedin Sweetheart Cottage Short Walk to Downtown

Dunedin house

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$383

Clearwater Beach 3-bedroom Waterfront Luxury Condo

Clearwater condo

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$320

Corner Cottage, 120 steps to the beach, Historic Beach House, sleeps 5, Pets ok

Clearwater cottage

1 bedroom / 1 bathroom / sleeps 5

“Great cozy home away from home.” We stayed in the Orleans bungalo apartment on July 15-18. It felt like we were at home. The apartment had lots of character and charm. Loved sitting outside on the terrace watching the free entertainment across the street , was it called the ship wrecked bar? I especially loved beiing able to go to the back alley and washing clothes. (I hope it belonged to the cottages property, if not then oops!) We utilized the kitchen and the gas grill out back on the patio.Everything was great and this cottage had plenty of space for two families. We met my cousins from Texas in Flordia for a vaca. We drove from Oklahoma. The flat screens worked great. I have no complaints about this place. I just want to say to all you all snotty people leaving negative comments.... Quit complaining or find somewhere else to stay. What exactly do you think you are getting when you hear the word "cottages" it's not going to have a bell hop and a maid that cleans up your messes daily. Maybe some of you never lived in 100 year old homes and only used to a lavish lifestyle. Obviously you spent your time in doors. not us we were at the beach the majority of the day until almost 9pm every night. I enjoyed my stay there. It was a good 3 day stay for us despite the rainy weather. Yet we still had fun.

Price per night from

$217

single family home one level, all one family homes community

New Port Richey house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$66

Avalon at Clearwater

Clearwater apartment

1 bedroom / 1 bathroom / sleeps 2

“Location,Location,Location” Terrific get-a-way. Quiet, comfortable ,very clean, has everything you could want .Very close to other locations such as Tampa ,Dunedin. Beautiful beaches. Fabulous sunsets. .Great restaurants within walking distances. Condo has a beautiful pool. Truly a paradise . A must rental.

Price per night from

$121

Waterfront Private Home with Pool! AMAZING HOME!

Hudson house

2 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 1 hour 33 minutes

Price per night from

$229

Gulf Front 6 bdrm pvt htd/pool slps up to 20

Crystal Beach house

6 bedrooms / 4 bathrooms / sleeps 21

Price per night from

$1,150

Beautifully updated Clearwater Condo- 20-25 Minutes to the Beach

Clearwater condo

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$189

Tropical Island Retreat-Private Waterfront

Tarpon Springs house

4 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$295

CLEARWATER LUXURY RESORT STYLE CONDO

Clearwater condo

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$171

Waterfront Island Pool Home with Hot Tub and Canoe!!

Tarpon Springs house

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 50 minutes

Price per night from

$315

Holiday House In Florida At A Lake

Port Richey house

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$152

Fabulous Resort Style Condo In Clearwater

Clearwater apartment

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$74

Luxury 3BR GulfFront "Grateful to be at the Gulf"

Hudson apartment

3 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$99

Viewing 38 of 595
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Top Destination reviews

Geodesic Dome
Wonderful trip

We booked a stay from Thursday to Sunday and it was so peaceful and beautiful. This location is worth the visit and the owners are so pleasant and take great care of their property. If your looking for a peaceful get away this is it ! … see more
Clearwater Florida area's best kept secret, GULF FRONT 80FT LAP POOL AND WIFI
Nice place to stay!

Beautiful place to enjoy all that Tarpon Springs area has to offer. Place is a good example of old Florida. Lovely pool to enjoy the picturesque view of the river and ocean. Stingrays, manatees and various fish species hang around the dock at varied times. Thank you Dianne for opening your home to us!see more

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