Some info has been automatically translated. Show original language

Caladesi Island vacation rentals

Book unique condos, vacation rentals, 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
Home in Dunedin
Wonderful family friendly home in Dunedin FL
Comfy Kid & Pet friendly Florida home, 15 minutes to Honeymoon Island, Caledesi State park & Clearwater Beach and Clearwater Aquarium. Large kitchen, dining area, & nice screened in back porch. Shopping malls, grocery store and pharmacies two blocks away. Take a stroll in fun Downtown Dunedin, go for a bike ride on the Pinellas Trail or play foosball and table games with the family. Short drive to Busch Gardens, Lowry Park Zoo or the Florida Aquarium. The yard is fenced in and quite spacious.
Oct 20 – 27
ﺩ.ﺇ477 per night
4.9 out of 5 average rating, 204 reviews
Guest favorite
Apartment in Clearwater
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 26 – Oct 3
ﺩ.ﺇ441 per night
4.99 out of 5 average rating, 346 reviews
Guest favorite
Guesthouse in Palm Harbor
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.
Jul 24 – 31
ﺩ.ﺇ375 per night
4.97 out of 5 average rating, 190 reviews

Popular amenities for Caladesi Island vacation rentals

Caladesi Island cabin rentals

Guest favorite
Cabin in Palmetto
Nautical Theme Cozy Log Cabin Near Skyway, 75, 275
Nov 11 – 18
ﺩ.ﺇ472 per night
4.97 out of 5 average rating, 124 reviews
Guest favorite
Cabin in Odessa
Cozy 1960’s Cabin in Gated Lake Community
Dec 21 – 28
ﺩ.ﺇ399 per night
4.96 out of 5 average rating, 54 reviews
Guest favorite
Cabin in Safety Harbor
Safety Harbor Cottage
Dec 10 – 17
ﺩ.ﺇ300 per night
5.0 out of 5 average rating, 13 reviews
Guest favorite
Cabin in Land O' Lakes
Tiny Lakefront Cabin
Jul 15 – 22
ﺩ.ﺇ374 per night
4.96 out of 5 average rating, 51 reviews
Superhost
Cabin in Seminole
Lakefront Vacation Cabin on Lake Seminole #406
Sep 17 – 24
ﺩ.ﺇ544 per night
4.67 out of 5 average rating, 15 reviews
Guest favorite
Cabin in Lutz
Lakehouse Suite & Renovated Vintage Camper
Aug 6 – 13
ﺩ.ﺇ665 per night
4.94 out of 5 average rating, 17 reviews
Superhost
Cabin in New Port Richey
Fisherman's Cabin
May 21 – 28
ﺩ.ﺇ264 per night
4.13 out of 5 average rating, 24 reviews
Cabin in Tampa
PineCone Cabin Getaway near Natl Park
Nov 4 – 11
ﺩ.ﺇ299 per night
4.79 out of 5 average rating, 57 reviews
Guest favorite
Cabin in Palm Harbor
Beautiful Cabin w/all the amenities! (Fauna)
Dec 10 – 17
ﺩ.ﺇ724 per night
5.0 out of 5 average rating, 5 reviews
Guest favorite
Cabin in Tampa
Sweet Tiny cabin
May 12 – 19
ﺩ.ﺇ290 per night
5.0 out of 5 average rating, 5 reviews
Guest favorite
Cabin in Odessa
Peaceful Lakefront Home. sleeps 10 Come and Relax
Aug 2 – 9
ﺩ.ﺇ999 per night
4.91 out of 5 average rating, 23 reviews
Cabin in Clearwater
Frenchy's Cottage 490 in Clearwater Beach
May 7 – 14
ﺩ.ﺇ1,401 per night
4.69 out of 5 average rating, 13 reviews

Caladesi Island house rentals

Guest favorite
Home in Clearwater Beach
The Cottage - 32 Steps to the Beach - Sleeps 2, drive to your door, Wifi, Grill. Just Steps from the beach.
Aug 20 – 27
ﺩ.ﺇ849 per night
4.93 out of 5 average rating, 158 reviews
Guest favorite
Home in Tarpon Springs
Tree House Treasure
Jul 4 – 11
ﺩ.ﺇ372 per night
4.95 out of 5 average rating, 167 reviews
Guest favorite
Home in Clearwater
Coastal Cottage B - Bikes Beach Items
Jan 13 – 20
ﺩ.ﺇ400 per night
4.89 out of 5 average rating, 112 reviews
Guest favorite
Home in Largo
Live Oak Lodge
Jul 19 – 26
ﺩ.ﺇ357 per night
4.92 out of 5 average rating, 337 reviews
Guest favorite
Home in Tarpon Springs
Our Gemini Place: Comfort & Charm in Old Tarpon
May 16 – 23
ﺩ.ﺇ408 per night
4.93 out of 5 average rating, 101 reviews
Guest favorite
Home in Dunedin
Barefoot Parrot House- Walk to Downtown & Water
Nov 16 – 23
ﺩ.ﺇ1,250 per night
4.97 out of 5 average rating, 227 reviews
Guest favorite
Home in Holiday
King Bed Luxury & Queen 2/1/1—Patio+Computer+3TVs
Apr 25 – May 2
ﺩ.ﺇ293 per night
4.94 out of 5 average rating, 139 reviews
Guest favorite
Home in Dunedin
Downtown Keylime Cottages 4
Apr 9 – 16
ﺩ.ﺇ966 per night
4.91 out of 5 average rating, 148 reviews
Guest favorite
Home in Clearwater
Beautiful renovated 2br home near Clearwater Beach
May 21 – 28
ﺩ.ﺇ479 per night
4.91 out of 5 average rating, 115 reviews
Guest favorite
Home in Dunedin
“Quintessential” 1926 Downtown Dunedin Cottage
Jun 22 – 29
ﺩ.ﺇ679 per night
4.89 out of 5 average rating, 222 reviews
Guest favorite
Home in Largo
Gem-3 miles to the Beach -king bed -free parking
Jul 16 – 23
ﺩ.ﺇ448 per night
4.97 out of 5 average rating, 105 reviews
Guest favorite
Home in Tarpon Springs
Historic Downtown Tarpon Springs Hidden Gem
May 6 – 13
ﺩ.ﺇ476 per night
4.97 out of 5 average rating, 123 reviews

Caladesi Island condominium rentals

Guest favorite
Condo in Indian Rocks Beach
Waterfront Condo w/ Boat dock, 2 min walk to beach
Nov 26 – Dec 3
ﺩ.ﺇ372 per night
4.79 out of 5 average rating, 222 reviews
Guest favorite
Condo in Largo
Modern and Cozy Condo 6 Minutes from the Beach !
Aug 11 – 18
ﺩ.ﺇ328 per night
4.89 out of 5 average rating, 178 reviews
Guest favorite
Condo in Redington Beach
NoCleaningFees/AmazingBeachCondo/AwesomeAmenities2
Jun 28 – Jul 5
ﺩ.ﺇ427 per night
4.97 out of 5 average rating, 245 reviews
Guest favorite
Condo in Redington Beach
Royal Orleans and Redington Beach ( Studio 203 )
Oct 17 – 24
ﺩ.ﺇ297 per night
4.91 out of 5 average rating, 105 reviews
Guest favorite
Condo in St. Pete Beach
Sunset Beach Condo in Treasure Island
Oct 17 – 24
ﺩ.ﺇ387 per night
4.91 out of 5 average rating, 199 reviews
Guest favorite
Condo in Redington Beach
SWEET BEACH RETREAT - REDINGTON BEACH FLORIDA
Sep 2 – 9
ﺩ.ﺇ290 per night
4.89 out of 5 average rating, 148 reviews
Guest favorite
Condo in Redington Beach
Beach Condo, Heated Pool, 2 Minute Walk to Ocean
Oct 8 – 15
ﺩ.ﺇ365 per night
4.94 out of 5 average rating, 356 reviews
Guest favorite
Condo in Redington Beach
StudioCondo 2minWalk to the beach, BBQ Pool. RO109
Oct 30 – Nov 6
ﺩ.ﺇ347 per night
4.9 out of 5 average rating, 218 reviews
Guest favorite
Condo in Clearwater
Amazing views on beachfront
Sep 14 – 21
ﺩ.ﺇ1,939 per night
4.91 out of 5 average rating, 212 reviews
Guest favorite
Condo in Palm Harbor
Lakeside 2- Bed Apartment Near Clearwater Beaches
Sep 1 – 8
ﺩ.ﺇ291 per night
4.8 out of 5 average rating, 156 reviews
Guest favorite
Condo in Indian Rocks Beach
Villa Al Golfo Pristine Waterfront Oasis
Jan 28 – Feb 4
ﺩ.ﺇ790 per night
4.99 out of 5 average rating, 106 reviews
Guest favorite
Condo in Indian Shores
1 BR direct beachfront, gorgeous sunsets!
Dec 8 – 15
ﺩ.ﺇ463 per night
4.96 out of 5 average rating, 142 reviews

Destinations to explore

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