Holiday Rentals

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586 Houses

Price per night from

$201

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

Great rentals within 20 miles that match your search

COZY RETREAT modern condo near Gulf of Mexico beaches

Clearwater condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

“Fabulous!” Owner was great! Condo is everything you need or want. Every detail is perfect. Pool was just steps away.

Price per night from

$160

COURTYARD VIEW modern condo near Gulf of Mexico beaches

Clearwater house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$172

BEACH-FRONT! April 2024 Availability!

Clearwater condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

Price per night from

$84

Harborview Grande 507 Beachy and family-friendly

Clearwater apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 50 minutes

Price per night from

$1,050

Tranquil by Belleair Beach/Largo

Largo house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$166

1BR Pool View Condo in Clearwater Florida

Clearwater condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“Outstanding as usual.” Second year staying at the Avalon. Great location! About 5 miles to the beach one way, and about 6.5 the other way. Everything needed is within walking distance. Pool is great if the beach isn't your thing. Excellent workout room.

Price per night from

$103

Amazing Sunset over Clearwater Beach

Clearwater condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$229

Luxury waterfront Condo Rooftop Terrace

Clearwater house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$566

Affordable Luxury Mediterranean Style Resort in Clearwater

Clearwater apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$95

Surfside Condos 303 Beachfront Condo

Clearwater apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 50 minutes

Price per night from

$1,225

440 West Condos 508-S Gulf Front Condo

Clearwater apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 50 minutes

Price per night from

$367

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

Clearwater apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 2

Responds fast! avg. 50 minutes

Price per night from

$179

Sunfish Flat Beachfront Condo 3 Beachfront Condo

Clearwater apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 50 minutes

Price per night from

$1,381

Harborview Grande 602 Beautiful Condo Hardwood floors

Clearwater apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 50 minutes

Price per night from

$1,415

Bayside Condos 18 Just Updated Waterfront

Clearwater apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 50 minutes

Price per night from

$126

Belle Harbor 603M Posh Pineapple

Clearwater apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 50 minutes

Price per night from

$343

Belle Harbor 1105M Fabulous Luxury 11th Floor View at Belle Harbor

Clearwater apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 50 minutes

Price per night from

$584

440 West Condos 1501-N Condo with a water view

Clearwater apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 50 minutes

Price per night from

$578

440 West Condos 1402-N Gorgeous Waterview Condo

Clearwater apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 50 minutes

Price per night from

$174

Bay Harbor 301 Beautiful Waterfront Condo

Clearwater apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Responds fast! avg. 50 minutes

Price per night from

$1,490

Belle Harbor 407M Luxury Clearwater Beach Condo

Clearwater apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 50 minutes

Price per night from

$317

Private Island Oasis on Gulf with Stunning Views

Hudson condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$172

Royal Marina | Avalon at Clearwater | Minutes to Clearwater Beach

Clearwater condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$206

440 West Condos 808-N Beautiful Water View

Clearwater apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 50 minutes

Price per night from

$155

Lovely Tropical Sunlit bedroom

Clearwater house

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Price per night from

$228

Quiet Waterfront Home, Gulf-access

Tarpon Springs house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$241

Mediterranean Lakefront Mansion

Tampa house

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 20

Price per night from

$1,138

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

Tampa house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$191

8 houses from beach and gulf in Clearwater beach

Clearwater house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$262

Coconut Beach House - Private Pool

Clearwater house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 12

Price per night from

$823

Art's Beach Retreat

Belleair Beach villa

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$286

Clearwater Beach Waterfront - With Private Rooftop Terrace

Clearwater townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$401

The Cobbles

Hudson villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 24 minutes

Price per night from

$174

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.

Responds fast! avg. 50 minutes

Price per night from

$54

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

Price per night from

$1,043

Bay Breeze House Waterfront home with pool

Clearwater house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Responds fast! avg. 50 minutes

Price per night from

$540

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