Clearwater, FL Vacation Rentals

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311 cottages

Perfecto's Retreat Unit #1

St. Petersburg cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Rental types Shared outdoor pool (unheated)

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Price per night from

$341

A Private, Spacious and Modern Home Away From Home. Heated Pool. Bikes, Boards,

Madeira Beach cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Responds fast! avg. 3 minutes

Match: Rental types Shared outdoor pool (unheated)

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Price per night from

$166

Leave Your Troubles Behind. Relaxation, Value, and Peace in the Heart of Madeira

Madeira Beach cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 3 minutes

Match: Rental types Shared outdoor pool (unheated)

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Price per night from

$132

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Lovely Tropical Sunlit bedroom

Clearwater house

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 of 2 match: Rental types, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$227

Beachy Clearwater is Great! Pets Welcome

Clearwater house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 3

1 of 2 match: Rental types, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$92

Clearwater Beach Condo 2 B|R fits 5-8 ppl

Clearwater apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 28 minutes

1 of 2 match: Rental types, Shared outdoor pool (unheated)

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Price per night from

$172

Clearwater Sugar Beach

Clearwater apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 1

1 of 2 match: Rental types, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$85

Casa Daniella

Clearwater house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 2

1 of 2 match: Rental types, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$200

Beautiful Boho Style Condo

Clearwater condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Rental types, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$216

1 of 2 match: Rental types, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$326

Clearwater Vacation Beach 2 B/R Condo fits 6ppl

Clearwater condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 28 minutes

1 of 2 match: Rental types, Shared outdoor pool (unheated)

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Price per night from

$149

Amazing Condo and Breathtaking Views!

Indian Rocks Beach condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

Responds fast! avg. 3 hours 36 minutes

1 of 2 match: Rental types, Shared outdoor pool (unheated)

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Price per night from

$599

Luxury waterfront Condo Rooftop Terrace

Clearwater house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Rental types, Shared outdoor pool (unheated)

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Price per night from

$565

Aqualea at Hyatt Regency, Clearwater Beach FL

Clearwater apartment

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 5

1 of 2 match: Rental types, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$343

Clearwater Beach Resort Apartment with Oceanview

Clearwater apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

Responds fast! avg. 3 hours 54 minutes

1 of 2 match: Rental types, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$422

Condo Penthouse with Pool And Hot Tub

Tampa condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Rental types, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$237

Bayside Condos 17 Waterfront Studio

Clearwater apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Responds fast! avg. 50 minutes

1 of 2 match: Rental types, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$99

Regatta Beach Club 414S '90 day min stay with 2 week lead time'

Clearwater condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 50 minutes

1 of 2 match: Rental types, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$103

Chateau 5W Beachfront on the Beautiful Belleair Beach

Belleair Beach apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 50 minutes

1 of 2 match: Rental types, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$154

Harborview Grande 507 Beachy and family-friendly

Clearwater apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 50 minutes

1 of 2 match: Rental types, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$1,048

Intercoastal 209 Water View from this Charming Condo

Indian Shores apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 50 minutes

1 of 2 match: Rental types, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$5,170

Surfside Condos 303 Beachfront Condo

Clearwater apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 50 minutes

1 of 2 match: Rental types, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$1,222

440 West Condos 1408-N Gulf Front Condo with amazing views

Clearwater apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 2

Responds fast! avg. 50 minutes

1 of 2 match: Rental types, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$178

Harborview Grande 602 Beautiful Condo Hardwood floors

Clearwater apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 50 minutes

1 of 2 match: Rental types, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$1,412

Bayside Condos 18 Just Updated Waterfront

Clearwater apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 50 minutes

1 of 2 match: Rental types, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$126

Bay Harbor 301 Beautiful Waterfront Condo

Clearwater apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Responds fast! avg. 50 minutes

1 of 2 match: Rental types, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$1,487

Brightwater Point 105 Grand Water Views

Clearwater apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

“Perfect in every way!” Perfect location; beautiful condo; everything we needed. If I could have a negative comment it would be that the couch was a little uncomfortable. I can't say enough about how perfect; we have made arrangements to return!

Responds fast! avg. 50 minutes

1 of 2 match: Rental types, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$1,041

Island Key Condos 303 Large Balcony overlooking Bay

Clearwater apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Amazing” We were first time renters and we're very anxious. We couldn't have been more impressed. There was so much space and the condo was spotless. The area was quiet and the apartment block was spotless. The pool was heated and spa was hot. The staff in the office were so nice and helpful made us feel really valued. Will definitely be returning and would highly recommend the rental company.

Responds fast! avg. 50 minutes

1 of 2 match: Rental types, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$279

Villas of Clearwater Beach 2B Renovated condo that is just Steps to the beach an

Clearwater apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 7

Responds fast! avg. 50 minutes

1 of 2 match: Rental types, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$209

Landmark Tower 1707 Charming 17th Floor Oceanfront Condo

Clearwater apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 50 minutes

1 of 2 match: Rental types, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$136

Madeira Towers 302 Beachfront 3 bedroom 2 bath at Madeira Towers

Madeira Beach condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 50 minutes

1 of 2 match: Rental types, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$386

Bay Harbor 501 Beautiful 5th Floor Waterfront Condo

Clearwater apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Responds fast! avg. 50 minutes

1 of 2 match: Rental types, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$882

Gulf Belleair Beach Condo 325 Condo located on Belleair Beach

Belleair Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 50 minutes

1 of 2 match: Rental types, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$133

Brightwater Point Condo 106 Amazing Water View Condo

Clearwater apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Responds fast! avg. 50 minutes

1 of 2 match: Rental types, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$559

Barefoot Beach Resort F110 Waterfront pool and short walk to the beach

Indian Shores condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Responds fast! avg. 50 minutes

1 of 2 match: Rental types, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$873

ROYAL REXHOST RESORTS – Madeira Beach Yacht Club (MBYCC)

Madeira Beach house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Rental types, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$160

ROYAL REXHOST RESORTS – Madeira Beach Yacht Club (MBYCC)

Madeira Beach house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Rental types, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$172

The Jitterbug Apt: Central 1 bedroom w pullout bed, 10 mins to DTSP pet friendly

Pinellas Park apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Rental types, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$172

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rentals in Clearwater

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