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Pink Gulfside Cottage, 100 steps to beach, Pet OK, Restored Beach House

Clearwater house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

Match: Rental types Swing set or jungle gym

All filters match

Price per night from

$286

Match: Rental types Swing set or jungle gym

All filters match

Price per night from

$424

BoHo Style Home [Playset, Patio / 5 min Clearwater Beach]

Clearwater house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

Match: Rental types Swing set or jungle gym

All filters match

Price per night from

$207

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Best Vacation Spot

Clearwater b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 of 2 match: Rental types, Swing set or jungle gym

1 of 2 filters match

Price per night from

$86

Luxurious Beachfront Condo at Redington Towers

Redington Shores condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Rental types, Swing set or jungle gym

1 of 2 filters match

Price per night from

$344

Lemon Cottage, Pets OK , 200 Steps to Beach

Clearwater cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Rental types, Swing set or jungle gym

1 of 2 filters match

Price per night from

$297

Steps from Beach, Pets OK, Sleeps 6, Clearwater Beach. 2 Bedrooms

Clearwater apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Rental types, Swing set or jungle gym

1 of 2 filters match

Price per night from

$378

“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.

1 of 2 match: Rental types, Swing set or jungle gym

1 of 2 filters match

Price per night from

$297

ROYAL REXHOST RESORTS – Madeira Beach Yacht Club (MBYCC)

Madeira Beach guest house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Rental types, Swing set or jungle gym

1 of 2 filters match

Price per night from

$172

Luxury waterfront Condo Rooftop Terrace

Clearwater house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Swing set or jungle gym, Rental types

1 of 2 filters match

Price per night from

$568

3br - Belleair beach vacation rental, 3bd/2bth

Tampa house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Swing set or jungle gym, Rental types

1 of 2 filters match

Price per night from

$192

8 houses from beach and gulf in Clearwater beach

Clearwater house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Swing set or jungle gym, Rental types

1 of 2 filters match

Price per night from

$263

Sandy Shores Beach House - Beachfront Home

Clearwater house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Swing set or jungle gym, Rental types

1 of 2 filters match

Price per night from

$626

Treasure Island Villa - Beachfront with a pool!

Treasure Island house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 14

1 of 2 match: Swing set or jungle gym, Rental types

1 of 2 filters match

Price per night from

$1,978

Clearwater Beach Cabana - Private Pool

Clearwater house

  • 7 bedrooms
  • 4 bathrooms
  • sleeps 26

1 of 2 match: Swing set or jungle gym, Rental types

1 of 2 filters match

Price per night from

$1,715

3 Palms Retreat - Beachfront

Indian Rocks Beach house

  • 7 bedrooms
  • 4 bathrooms
  • sleeps 16

1 of 2 match: Swing set or jungle gym, Rental types

1 of 2 filters match

Price per night from

$1,583

Exclusive Isla Bonita - Private Pool - Steps from the sand

Indian Rocks Beach house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

1 of 2 match: Swing set or jungle gym, Rental types

1 of 2 filters match

Price per night from

$922

Beachfront GULF Cottage at beautiful Sandy Shores on Gulf of Mexico

Indian Rocks Beach house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 1 hour 4 minutes

1 of 2 match: Swing set or jungle gym, Rental types

1 of 2 filters match

Price per night from

$300

Alice's Beach Bungalows 2 bedroom

Treasure Island house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

“A perfect spot for us and for our golden retriever!” What a great place to enjoy the beauty of Treasure Island. The bungalow that we stayed in was wonderful...clean, a well stocked kitchen, beach towels, a great backyard. Susan, the owner, was also great to work with on every level. She was attentive, often checking in on us to make sure all was going great with our stay. She was also responsive to our rental needs and responded immediately if we had a question, etc.. She also embraced our golden retriever and he, too, immediately became fast friends with Susan. This bungalow is literally a block from the beach, a short walk over the bridge to John's Pass and close to grocery shopping, lots of great restaurants right on the beach, etc.. A great experience and we will definitely plan to stay at this bungalow again!

1 of 2 match: Swing set or jungle gym, Rental types

1 of 2 filters match

Price per night from

$316

X Alice's Beach Bungalows 2 bdrm 500' to Beach!

Treasure Island house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Swing set or jungle gym, Rental types

1 of 2 filters match

Price per night from

$373

One Of The Last One Story Beach Houses

Indian Shores house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Swing set or jungle gym, Rental types

1 of 2 filters match

Price per night from

$328

Seminole Vacation House Spacious Vacation House

Seminole house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

Responds fast! avg. 50 minutes

1 of 2 match: Swing set or jungle gym, Rental types

1 of 2 filters match

Price per night from

$107

Tranquil by Belleair Beach/Largo

Largo house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Swing set or jungle gym, Rental types

1 of 2 filters match

Price per night from

$167

Private Waterfront Home, Resort & Marina Sleeps 18

Madeira Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 18

1 of 2 match: Swing set or jungle gym, Rental types

1 of 2 filters match

Price per night from

$153

Bay Breeze House Waterfront home with pool

Clearwater house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Responds fast! avg. 50 minutes

1 of 2 match: Swing set or jungle gym, Rental types

1 of 2 filters match

Price per night from

$542

3 bedroom, 2 bath home, just steps to the beach

Treasure Island house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“What a great week we had” We recently had a family reunion at this beach house. There were eight of us and there was plenty of room. The house was a wonderful place and we really enjoyed morning coffee around the island in the kitchen and s'mores in the evening on the back deck around the fire pit. Several times we grabbed a glass of wine and walked to the beach to watch the sunset and even saw a few dolphins. The area seemed to have a lot of events happening nearby, sand sculptures on the beach, shopping at a restored fishing village with several unique shops, bands on the sands and fireworks. The oversized wrap around deck added extra room to what already felt like a spacious house. The house is beautiful and we look forward to vacationing there again.

1 of 2 match: Swing set or jungle gym, Rental types

1 of 2 filters match

Price per night from

$459

Exclusive Tropical Retreat in Sunny Clearwater Bea

Clearwater house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

1 of 2 match: Swing set or jungle gym, Rental types

1 of 2 filters match

Price per night from

$481

Dolphin House Short Walk To The Beach

Clearwater house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

Responds fast! avg. 50 minutes

1 of 2 match: Swing set or jungle gym, Rental types

1 of 2 filters match

Price per night from

$359

INTRACOASTAL GETAWAY HOME

Indian Shores house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

1 of 2 match: Swing set or jungle gym, Rental types

1 of 2 filters match

Price per night from

$293

PRIVATE BEACH OPEN** Beachfront bungalow 4BR *Htd POOL*Pet

Indian Shores house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

“A wonderful place to be!” Our rental was right on the pool/beach. It was perfect! Gorgeous pool and the beach - beautiful, private - everything you could want. The cottages were spacious, clean and kitschy. They had everything you needed. You could tell good people stayed there as everything was well kept and stocked. The owner, Liz, was lovely and even though we had no pets, every pup there was well behaved and everyone was respectful of the rules. The people staying at the other cottages were wonderful and had stayed there before. Obviously Liz knows what she’s doing . My parents also stayed with us and both of them loved the place. The beds were very comfortable which doesn’t always happen in rentals. Hoping to see you next year! Cheers!

1 of 2 match: Swing set or jungle gym, Rental types

1 of 2 filters match

Price per night from

$488

Intracoastal Indian Rocks Beach House

Indian Rocks Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

1 of 2 match: Swing set or jungle gym, Rental types

1 of 2 filters match

Price per night from

$459

Beachy "Margaritaville Pool home", 3 BR, 2 Bath

Clearwater house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

1 of 2 match: Swing set or jungle gym, Rental types

1 of 2 filters match

Price per night from

$488

Dunedin Relax in our Updated condo

Dunedin house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Swing set or jungle gym, Rental types

1 of 2 filters match

Price per night from

$89

Relaxing Getaway,Compleatly Renovated*New furnishing*Private Heated Pool Home*

Redington Beach house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Swing set or jungle gym, Rental types

1 of 2 filters match

Price per night from

$458

Tropical Treasure Villa - Giant spa and steps from the beach!

Redington Beach house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 14

1 of 2 match: Swing set or jungle gym, Rental types

1 of 2 filters match

Price per night from

$943

Tranquil Tarpon Cottage - Giant Swim Spa

Redington Beach house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 13

1 of 2 match: Swing set or jungle gym, Rental types

1 of 2 filters match

Price per night from

$922

Starfish Gulf Front Two Bedroom Cottage

Madeira Beach house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Swing set or jungle gym, Rental types

1 of 2 filters match

Price per night from

$196

Brightwater Blue 158-4 3 Floors of luxury with beautiful water views

Clearwater house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 50 minutes

1 of 2 match: Swing set or jungle gym, Rental types

1 of 2 filters match

Price per night from

$5,197

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