Caladesi Island vacation rentals
Book unique vacation rentals, houses, and more on Airbnb
Top-rated vacation rentals in Caladesi Island
Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.
Apartment in Clearwater
4.99 out of 5 average rating, 347 reviewsPrivate studio attached to house. Pool&bikes
Completely private studio, bathroom & your own private saltwater pool. Studio attached to house. No cleaning fee. 1 block west to Edgewater trail. Beautiful sunsets on water. 1 block east to famous Pinellas trail. Stroll to downtown Dunedin or TD Stadium. Cruiser bikes provided. Drive, Uber, trolley or bike 4.5 miles to Clearwater Beach or Honeymoon Island. Near restaurants, shops, dancing, kayaking, fishing, boating, biking, baseball, etc! Space is not appropriate for under 18, pets, parties.
Sep 21 – 28
Home in Dunedin
4.96 out of 5 average rating, 204 reviewsFLOH - delightful days in Dunedin!
Cute quaint house with 2 bedrooms, 1 bath, located in downtown Dunedin Florida. All furniture in the house is new. Bathroom is newly remodeled, and includes a shower with a jet tub. Cozy family room with 60" flat screen smart TV, and sleeper sofa. We have a desk, and elliptical machine, along with a comfy chair for reading/relaxing in the extra room on the back. The kitchen is fully functional, with most conveniences of home. Come and enjoy delightful Dunedin, and have the time of your life!
Jul 13 – 20
Guesthouse in Palm Harbor
4.97 out of 5 average rating, 193 reviewsPrivate Suite, 1 bedroom, 1 bathroom, pool, patio
Private suite located in Palm Harbor with king-size bed, Split unit A/C Amenities include: Large Bathroom with Jacuzzi, Walk-in Shower, Double sink Vanity. Access to Patio, Swimming Pool , Backyard and Sundeck. Room includes small refrigerator/freezer, Microwave, Coffee maker, Espresso, Iron and much more. Bistro set in room. Private entrances to room and patio/backyard. Cable TV, Netflix and Wi-Fi included. Centrally located to Restaurants and shopping. 10 mins. to the beach/Pinellas Trail.
Jun 4 – 11
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Caladesi Island vacation rentals
Caladesi Island house rentals
Home in Clearwater Beach
4.93 out of 5 average rating, 157 reviewsThe Cottage - 32 Steps to the Beach - Sleeps 2, drive to your door, Wifi, Grill. Just Steps from the beach.
Jul 19 – 26
Home in Tarpon Springs
4.95 out of 5 average rating, 171 reviewsTree House Treasure
May 31 – Jun 7
Home in Dunedin
4.91 out of 5 average rating, 150 reviewsDowntown Keylime Cottages 4
Jun 12 – 19
Home in Clearwater
4.89 out of 5 average rating, 112 reviewsCoastal Cottage B - Bikes Beach Items
Aug 14 – 21
Home in Largo
4.87 out of 5 average rating, 227 reviewsBanyan Bungalow
Jul 29 – Aug 5
Home in Dunedin
4.99 out of 5 average rating, 99 reviewsDowntown Dunedin, Trail, Marina, Beach, Park
Jul 20 – 27
Home in Dunedin
4.97 out of 5 average rating, 227 reviewsBarefoot Parrot House- Walk to Downtown & Water
Oct 3 – 10
Home in Clearwater
4.91 out of 5 average rating, 116 reviewsBeautiful renovated 2br home near Clearwater Beach
Jun 14 – 21
Home in Dunedin
4.9 out of 5 average rating, 204 reviewsWonderful family friendly home in Dunedin FL
Nov 25 – Dec 2
Home in Tarpon Springs
4.97 out of 5 average rating, 124 reviewsHistoric Downtown Tarpon Springs Hidden Gem
Aug 14 – 21
Home in Tarpon Springs
4.93 out of 5 average rating, 101 reviewsOur Gemini Place: Comfort & Charm in Old Tarpon
Jul 19 – 26
Home in Largo
4.9 out of 5 average rating, 149 reviewsQuaint Cottage 5 miles to the beaches
Jan 9 – 16
Caladesi Island beach vacation rentals
Condo in Redington Beach
4.97 out of 5 average rating, 455 reviewsAmazingBeachCondo/NoCleaningFee/AwesomeAmenities
Nov 9 – 16
Apartment in Dunedin
4.99 out of 5 average rating, 198 reviewsTropical Paradise
Aug 21 – 28
Guest suite in Safety Harbor
4.99 out of 5 average rating, 199 reviewsSuite Outlook-Upstairs unit with Spectacular views
Mar 19 – 26
Apartment in Treasure Island
4.92 out of 5 average rating, 157 reviewsTreasure Island Beach Apartment #1
Nov 30 – Dec 7
Cottage in Dunedin
5.0 out of 5 average rating, 224 reviewsDowntown Dunedin Historic Orange Blossom Cottage 1
May 13 – 20
Guest suite in Dunedin
4.95 out of 5 average rating, 180 reviewsKrō Haus
Jul 6 – 13
Apartment in Tarpon Springs
4.99 out of 5 average rating, 188 reviewsClassic Hemingway Style 1 BR apt in Tarpon Springs
Jun 18 – 25
Cottage in Indian Rocks Beach
4.93 out of 5 average rating, 175 reviewsKooky Coconut Cottage, Indian Rocks Beach
Dec 13 – 20
Condo in Redington Beach
4.91 out of 5 average rating, 107 reviewsRoyal Orleans and Redington Beach ( Studio 203 )
Dec 8 – 15
Guesthouse in Gulfport
4.93 out of 5 average rating, 720 reviewsgraceful haven...
Sep 16 – 23
Guesthouse in Safety Harbor
4.92 out of 5 average rating, 224 reviewsTiny House Downtown, Superb Location
Jul 14 – 21
Apartment in Clearwater
4.95 out of 5 average rating, 150 reviewsPrivate Apt, Beach 2 mi, Steps to Park & Downtown
Aug 20 – 27
Beach house rentals in Caladesi Island
Home in Clearwater
5.0 out of 5 average rating, 109 reviewsBeach House
May 6 – 13
Home in Belleair Beach
4.96 out of 5 average rating, 163 reviewsBungalow on Private Beach Clearwater Bellair Beach
Oct 20 – 27
Home in Clearwater Beach
4.97 out of 5 average rating, 191 reviewsClearwater Beach Townhome w/Game Room & Boat Slip!
Sep 20 – 27
Home in Largo
4.97 out of 5 average rating, 105 reviewsGem-3 miles to the Beach -king bed -free parking
Aug 13 – 20
Home in Indian Rocks Beach
4.86 out of 5 average rating, 302 reviewsStunning views! Spot dolphins from the pool!
Dec 26 – Jan 2
Home in Tarpon Springs
4.98 out of 5 average rating, 107 reviewsHeated Pool, Close to Beaches!
Aug 27 – Sep 3
Home in Gulfport
4.91 out of 5 average rating, 128 reviewsGecko Cottage
Jul 26 – Aug 2
Home in Tampa
4.78 out of 5 average rating, 221 reviews*Waterfront* Kayaks & Bikes - Papa’s Rustic Cabin
May 17 – 24
Home in Indian Rocks Beach
4.95 out of 5 average rating, 115 reviewsBig 1/1 Beach house w/ Sunset Balcony
Oct 13 – 20
Home in Palm Harbor
4.95 out of 5 average rating, 157 reviews*Family Paradise with Pool in Crystal Beach*
Oct 17 – 24
Home in Largo
4.83 out of 5 average rating, 130 reviewsBeautiful Spacious Safe Clean & 7mins to the Beach
Aug 30 – Sep 6
Home in Indian Rocks Beach
4.89 out of 5 average rating, 115 reviewsB - BEACH HOUSE 3 MIN WALK TO THE BEACH
Sep 14 – 21
Destinations to explore
- Tampa Vacation rentals
- Anna Maria Island Vacation rentals
- Sarasota Vacation rentals
- Kissimmee Vacation rentals
- Orlando Vacation rentals
- Naples Vacation rentals
- West Palm Beach Vacation rentals
- Boca Raton Vacation rentals
- Fort Lauderdale Vacation rentals
- Miami Vacation rentals
- Miami Beach Vacation rentals
- Key West Vacation rentals
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom