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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.

Guest favorite

Apartment in Clearwater

4.99 out of 5 average rating, 347 reviews

Private 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

G$28,682 GYD per night
Guest favorite

Home in Dunedin

4.96 out of 5 average rating, 204 reviews

FLOH - 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

G$26,078 GYD per night
Guest favorite

Guesthouse in Palm Harbor

4.97 out of 5 average rating, 193 reviews

Private 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

G$21,851 GYD per night

Popular amenities for Caladesi Island vacation rentals

Caladesi Island house rentals

Guest favorite

Home in Clearwater Beach

4.93 out of 5 average rating, 157 reviews

The Cottage - 32 Steps to the Beach - Sleeps 2, drive to your door, Wifi, Grill. Just Steps from the beach.

Jul 19 – 26

G$55,507 GYD per night
Guest favorite

Home in Tarpon Springs

4.95 out of 5 average rating, 171 reviews

Tree House Treasure

May 31 – Jun 7

G$24,909 GYD per night
Guest favorite

Home in Dunedin

4.91 out of 5 average rating, 150 reviews

Downtown Keylime Cottages 4

Jun 12 – 19

G$41,046 GYD per night
Guest favorite

Home in Clearwater

4.89 out of 5 average rating, 112 reviews

Coastal Cottage B - Bikes Beach Items

Aug 14 – 21

G$24,043 GYD per night
Guest favorite

Home in Largo

4.87 out of 5 average rating, 227 reviews

Banyan Bungalow

Jul 29 – Aug 5

G$23,106 GYD per night
Guest favorite

Home in Dunedin

4.99 out of 5 average rating, 99 reviews

Downtown Dunedin, Trail, Marina, Beach, Park

Jul 20 – 27

G$38,876 GYD per night
Guest favorite

Home in Dunedin

4.97 out of 5 average rating, 227 reviews

Barefoot Parrot House- Walk to Downtown & Water

Oct 3 – 10

G$81,115 GYD per night
Guest favorite

Home in Clearwater

4.91 out of 5 average rating, 116 reviews

Beautiful renovated 2br home near Clearwater Beach

Jun 14 – 21

G$27,602 GYD per night
Guest favorite

Home in Dunedin

4.9 out of 5 average rating, 204 reviews

Wonderful family friendly home in Dunedin FL

Nov 25 – Dec 2

G$41,287 GYD per night
Guest favorite

Home in Tarpon Springs

4.97 out of 5 average rating, 124 reviews

Historic Downtown Tarpon Springs Hidden Gem

Aug 14 – 21

G$29,687 GYD per night
Guest favorite

Home in Tarpon Springs

4.93 out of 5 average rating, 101 reviews

Our Gemini Place: Comfort & Charm in Old Tarpon

Jul 19 – 26

G$27,110 GYD per night
Superhost

Home in Largo

4.9 out of 5 average rating, 149 reviews

Quaint Cottage 5 miles to the beaches

Jan 9 – 16

G$23,591 GYD per night

Caladesi Island beach vacation rentals

Guest favorite

Condo in Redington Beach

4.97 out of 5 average rating, 455 reviews

AmazingBeachCondo/NoCleaningFee/AwesomeAmenities

Nov 9 – 16

G$22,599 GYD per night
Guest favorite

Apartment in Dunedin

4.99 out of 5 average rating, 198 reviews

Tropical Paradise

Aug 21 – 28

G$39,479 GYD per night
Guest favorite

Guest suite in Safety Harbor

4.99 out of 5 average rating, 199 reviews

Suite Outlook-Upstairs unit with Spectacular views

Mar 19 – 26

G$21,041 GYD per night
Guest favorite

Apartment in Treasure Island

4.92 out of 5 average rating, 157 reviews

Treasure Island Beach Apartment #1

Nov 30 – Dec 7

G$26,608 GYD per night
Guest favorite

Cottage in Dunedin

5.0 out of 5 average rating, 224 reviews

Downtown Dunedin Historic Orange Blossom Cottage 1

May 13 – 20

G$42,493 GYD per night
Guest favorite

Guest suite in Dunedin

4.95 out of 5 average rating, 180 reviews

Krō Haus

Jul 6 – 13

G$34,803 GYD per night
Guest favorite

Apartment in Tarpon Springs

4.99 out of 5 average rating, 188 reviews

Classic Hemingway Style 1 BR apt in Tarpon Springs

Jun 18 – 25

G$27,206 GYD per night
Guest favorite

Cottage in Indian Rocks Beach

4.93 out of 5 average rating, 175 reviews

Kooky Coconut Cottage, Indian Rocks Beach

Dec 13 – 20

G$37,259 GYD per night
Guest favorite

Condo in Redington Beach

4.91 out of 5 average rating, 107 reviews

Royal Orleans and Redington Beach ( Studio 203 )

Dec 8 – 15

G$19,617 GYD per night
Guest favorite

Guesthouse in Gulfport

4.93 out of 5 average rating, 720 reviews

graceful haven...

Sep 16 – 23

G$23,811 GYD per night
Guest favorite

Guesthouse in Safety Harbor

4.92 out of 5 average rating, 224 reviews

Tiny House Downtown, Superb Location

Jul 14 – 21

G$18,367 GYD per night
Guest favorite

Apartment in Clearwater

4.95 out of 5 average rating, 150 reviews

Private Apt, Beach 2 mi, Steps to Park & Downtown

Aug 20 – 27

G$24,251 GYD per night

Beach house rentals in Caladesi Island

Guest favorite

Home in Clearwater

5.0 out of 5 average rating, 109 reviews

Beach House

May 6 – 13

G$121,548 GYD per night
Guest favorite

Home in Belleair Beach

4.96 out of 5 average rating, 163 reviews

Bungalow on Private Beach Clearwater Bellair Beach

Oct 20 – 27

G$57,414 GYD per night
Superhost

Home in Clearwater Beach

4.97 out of 5 average rating, 191 reviews

Clearwater Beach Townhome w/Game Room & Boat Slip!

Sep 20 – 27

G$147,586 GYD per night
Guest favorite

Home in Largo

4.97 out of 5 average rating, 105 reviews

Gem-3 miles to the Beach -king bed -free parking

Aug 13 – 20

G$33,103 GYD per night
Superhost

Home in Indian Rocks Beach

4.86 out of 5 average rating, 302 reviews

Stunning views! Spot dolphins from the pool!

Dec 26 – Jan 2

G$181,741 GYD per night
Guest favorite

Home in Tarpon Springs

4.98 out of 5 average rating, 107 reviews

Heated Pool, Close to Beaches!

Aug 27 – Sep 3

G$60,213 GYD per night
Guest favorite

Home in Gulfport

4.91 out of 5 average rating, 128 reviews

Gecko Cottage

Jul 26 – Aug 2

G$19,617 GYD per night
Guest favorite

Home in Tampa

4.78 out of 5 average rating, 221 reviews

*Waterfront* Kayaks & Bikes - Papa’s Rustic Cabin

May 17 – 24

G$35,046 GYD per night
Guest favorite

Home in Indian Rocks Beach

4.95 out of 5 average rating, 115 reviews

Big 1/1 Beach house w/ Sunset Balcony

Oct 13 – 20

G$34,485 GYD per night
Guest favorite

Home in Palm Harbor

4.95 out of 5 average rating, 157 reviews

*Family Paradise with Pool in Crystal Beach*

Oct 17 – 24

G$142,743 GYD per night
Guest favorite

Home in Largo

4.83 out of 5 average rating, 130 reviews

Beautiful Spacious Safe Clean & 7mins to the Beach

Aug 30 – Sep 6

G$26,202 GYD per night
Guest favorite

Home in Indian Rocks Beach

4.89 out of 5 average rating, 115 reviews

B - BEACH HOUSE 3 MIN WALK TO THE BEACH

Sep 14 – 21

G$33,688 GYD per night

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Pinellas County
  5. Dunedin
  6. Caladesi Island