Holiday rentals near Calusa Heritage Trail
We found 10,168 holiday rentals — enter your dates for availability
Choose the perfect holiday rental within close proximity to Calusa Heritage Trail. Holiday homes offer the amenities that you expect for you and your friends, family or even pets, such as a fireplace and garden. At the end of the day, you're sure to find a property to rent for everyone's needs, including a place that's non-smoking or offers accessibility.
Holiday rentals with weekly discounts - Calusa Heritage Trail
Showing deals for:3 Oct - 10 Oct
Image gallery for Beach Cottage on Private Little Gasparilla Island, relax & unwind!
9.89.8 out of 10 rating
Exceptional
(23 reviews)
Beach Cottage on Private Little Gasparilla Island, relax & unwind!
Placida, FL
8% off
Price is NZ$3,904
NZ$3,904
NZ$558 per night
includes taxes & fees
Image gallery for Newly listed, beautiful 2-bedroom, 2 bathroom condo in charming Boca Grande.
1010 out of 10 rating
Exceptional
(13 reviews)
Newly listed, beautiful 2-bedroom, 2 bathroom condo in charming Boca Grande.
Placida, FL
8% off
Price is NZ$6,279
NZ$6,279
NZ$897 per night
includes taxes & fees
Image gallery for Special:10-15% Discount! Book 2025 w/private pool, elevator, ocean view!
1010 out of 10 rating
Exceptional
(12 reviews)
Special:10-15% Discount! Book 2025 w/private pool, elevator, ocean view!
Captiva, FL
10% off
Price is NZ$7,976
NZ$7,976
NZ$1,139 per night
includes taxes & fees
Image gallery for Seahorse Suites #4. A Perfect Beach Getaway!
9.29.2 out of 10 rating
Wonderful
(5 reviews)
Seahorse Suites #4. A Perfect Beach Getaway!
Sanibel, FL
8% off
Price is NZ$4,457
NZ$4,457
NZ$637 per night
includes taxes & fees
Image gallery for Luxury Villa on main Rotonda canal
9.89.8 out of 10 rating
Exceptional
(55 reviews)
Luxury Villa on main Rotonda canal
Rotonda West, FL
17% off
Price is NZ$2,447
NZ$2,447
NZ$350 per night
includes taxes & fees
Image gallery for Beach front 1b/1b condo. Amazing Sunsets and Resort Amenities
1010 out of 10 rating
Exceptional
(16 reviews)
Beach front 1b/1b condo. Amazing Sunsets and Resort Amenities
Fort Myers, FL
8% off
Price is NZ$5,407
NZ$5,407
NZ$772 per night
includes taxes & fees
Image gallery for Spacious "Crab Cakes" Cottage on N. Captiva Island,FL with GolfCart and Starlink
8.88.8 out of 10 rating
Excellent
(11 reviews)
Spacious "Crab Cakes" Cottage on N. Captiva Island,FL with GolfCart and Starlink
Captiva, FL
12% off
Price is NZ$4,640
NZ$4,640
NZ$663 per night
includes taxes & fees
Image gallery for Perfect Oasis Retreat !Luxury NEW Built Home with Private Heated Pool, Games
9.49.4 out of 10 rating
Exceptional
(6 reviews)
Perfect Oasis Retreat !Luxury NEW Built Home with Private Heated Pool, Games
Cape Coral, FL
7% off
Price is NZ$3,186
NZ$3,186
NZ$455 per night
includes taxes & fees
Image gallery for Villa South Palms returns! Gulf-access with Southwest facing pool is back!
9.89.8 out of 10 rating
Exceptional
(31 reviews)
Villa South Palms returns! Gulf-access with Southwest facing pool is back!
Cape Coral, FL
6% off
Price is NZ$2,058
NZ$2,058
NZ$294 per night
includes taxes & fees
Image gallery for Secluded Beach House, steps to Sandy Beach on LGI with a shared dock!🏖️🎣
1010 out of 10 rating
Exceptional
(5 reviews)
Secluded Beach House, steps to Sandy Beach on LGI with a shared dock!🏖️🎣
Placida, FL
7% off
Price is NZ$3,554
NZ$3,554
NZ$508 per night
includes taxes & fees
Image gallery for SANTA CLARA! Coastal, modern 3BR ESCAPE, harbor view, boat slip, CLUB access
1010 out of 10 rating
Exceptional
(6 reviews)
SANTA CLARA! Coastal, modern 3BR ESCAPE, harbor view, boat slip, CLUB access
Captiva, FL
7% off
Price is NZ$4,444
NZ$4,444
NZ$635 per night
includes taxes & fees
Image gallery for SERENITY NOW~1 Min. To BEACH!-SCREENED-IN HEATED POOL-2 Carts-4&6, Island Club
9.69.6 out of 10 rating
Exceptional
(33 reviews)
SERENITY NOW~1 Min. To BEACH!-SCREENED-IN HEATED POOL-2 Carts-4&6, Island Club
Captiva, FL
8% off
Price is NZ$9,510
NZ$9,510
NZ$1,359 per night
includes taxes & fees
Image gallery for The Blue Marlin - Beachfront Oasis with Private Beachside Pool & Boat Dock
1010 out of 10 rating
Exceptional
(81 reviews)
The Blue Marlin - Beachfront Oasis with Private Beachside Pool & Boat Dock
Captiva, FL
8% off
Price is NZ$12,779
NZ$12,779
NZ$1,826 per night
includes taxes & fees
Image gallery for 2024 Winter still Available Waterfront corner lot-Heated Pool
1010 out of 10 rating
Exceptional
(36 reviews)
2024 Winter still Available Waterfront corner lot-Heated Pool
Punta Gorda, FL
14% off
Price is NZ$2,282
NZ$2,282
NZ$326 per night
includes taxes & fees
Image gallery for Tranquil Beach Cottage with Private Heated Pool on Secluded Palm Island
9.89.8 out of 10 rating
Exceptional
(71 reviews)
Tranquil Beach Cottage with Private Heated Pool on Secluded Palm Island
Placida, FL
8% off
Price is NZ$4,120
NZ$4,120
NZ$589 per night
includes taxes & fees
Image gallery for 20% Discount on 6-Month Advanced Bookings and 10% Discount Last Minute Bookings
1010 out of 10 rating
Exceptional
(13 reviews)
20% Discount on 6-Month Advanced Bookings and 10% Discount Last Minute Bookings
Rotonda West, FL
7% off
Price is NZ$2,710
NZ$2,710
NZ$387 per night
includes taxes & fees
Image gallery for Relax in Paradise: 2-Bedroom Island Retreat with private Pool & Golf Cart!
1010 out of 10 rating
Exceptional
(12 reviews)
Relax in Paradise: 2-Bedroom Island Retreat with private Pool & Golf Cart!
Captiva, FL
12% off
Price is NZ$5,578
NZ$5,578
NZ$797 per night
includes taxes & fees
Image gallery for “Salt of the Sea” - Beachfront and Pet Friendly!
1010 out of 10 rating
Exceptional
(9 reviews)
“Salt of the Sea” - Beachfront and Pet Friendly!
Placida, FL
6% off
Price is NZ$5,413
NZ$5,413
NZ$773 per night
includes taxes & fees
Image gallery for Dream house near the beach, private pool, steps from the beach!
9.49.4 out of 10 rating
Exceptional
(25 reviews)
Dream house near the beach, private pool, steps from the beach!
Captiva, FL
8% off
Price is NZ$8,917
NZ$8,917
NZ$1,274 per night
includes taxes & fees
Image gallery for Tiki Life ! Relax and Enjoy w/m discount! Close to beaches without the costs!!
1010 out of 10 rating
Exceptional
(43 reviews)
Tiki Life ! Relax and Enjoy w/m discount! Close to beaches without the costs!!
Englewood, FL
13% off
Price is NZ$1,436
NZ$1,436
NZ$205 per night
includes taxes & fees
Image gallery for The Cozy Coconut~2Bd~2Ba~PRIVATE POOL~GOLF COURSE VIEW~NEARBY BEACHES
9.29.2 out of 10 rating
Wonderful
(9 reviews)
The Cozy Coconut~2Bd~2Ba~PRIVATE POOL~GOLF COURSE VIEW~NEARBY BEACHES
Rotonda West, FL
8% off
Price is NZ$2,096
NZ$2,096
NZ$299 per night
includes taxes & fees
Image gallery for Spacious 5-bedroom house in lovely Rotonda West with fast WiFi and Private Pool
1010 out of 10 rating
Exceptional
(12 reviews)
Spacious 5-bedroom house in lovely Rotonda West with fast WiFi and Private Pool
Rotonda West, FL
10% off
Price is NZ$3,101
NZ$3,101
NZ$443 per night
includes taxes & fees
Image gallery for DIRECT SAIL BOATS -GULF Access 5 bedroom 3 bath , Villa stunning View, sleep 11
9.29.2 out of 10 rating
Wonderful
(64 reviews)
DIRECT SAIL BOATS -GULF Access 5 bedroom 3 bath , Villa stunning View, sleep 11
Cape Coral, FL
5% off
Price is NZ$4,347
NZ$4,347
NZ$621 per night
includes taxes & fees
Image gallery for Luxury waterfront with heated- saltwater pool
9.89.8 out of 10 rating
Exceptional
(13 reviews)
Luxury waterfront with heated- saltwater pool
Cape Coral, FL
6% off
Price is NZ$2,368
NZ$2,368
NZ$338 per night
includes taxes & fees
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Find the best place to stay - Calusa Heritage Trail
Showing deals for: 1 Oct - 4 Oct
The Suites at Fishermen’s Village- 2 Bedroom Suites
Sleeps 4 · 2 bedrooms
9.89.8 out of 10
Exceptionalexceptional
928 reviews(928 reviews)
The current price is NZ$1,121
NZ$1,121
for 3 nights, 1 apartment
NZ$374 per night
includes taxes & fees
North Captiva Point House - Boat/Water Taxi Only **NEWLY RENOVATED **
Sleeps 6 · 2 bedrooms · 1 bathroom
9.69.6 out of 10
Exceptionalexceptional
97 reviews(97 reviews)
The current price is NZ$2,135
NZ$2,135
for 3 nights, 1 home
NZ$712 per night
includes taxes & fees
Salty Mermaid. Beach House on Little Gasparilla Island. Come get salty!
Sleeps 6 · 3 bedrooms · 2+ bathrooms
1010 out of 10
Exceptionalexceptional
3 reviews(3 reviews)
The current price is NZ$1,924
NZ$1,924
for 3 nights, 1 home
NZ$641 per night
includes taxes & fees
Pet-Friendly / Family-Friendly Waterfront Vacation Rental + Free Boat Dockage!
Sleeps 4
9.49.4 out of 10
Exceptionalexceptional
44 reviews(44 reviews)
The current price is NZ$848
NZ$848
for 3 nights, 1 home
NZ$283 per night
includes taxes & fees
Little Gasparilla Island - Gulf view, golf cart, ferry, pool, boat dock, parking
Sleeps 6 · 2 bedrooms · 2 bathrooms
9.89.8 out of 10
Exceptionalexceptional
87 reviews(87 reviews)
The current price is NZ$2,023
NZ$2,023
for 3 nights, 1 apartment
NZ$674 per night
includes taxes & fees
Welcome to THE HIVE. A hub for peace and relaxation. DIRECT GULF views
Sleeps 6 · 3 bedrooms · 3 bathrooms
1010 out of 10
Exceptionalexceptional
2 reviews(2 reviews)
The current price is NZ$3,324
NZ$3,324
for 3 nights, 1 home
NZ$1,108 per night
includes taxes & fees
Top rated rentals - Calusa Heritage Trail
Relaxing Angler's Club Townhome
1010 out of 10
Exceptionalexceptional
22 reviews(22 reviews)
Quiet, beautiful and clean. Overlooking the water. Rhonda the property manager was very helpful and made sure that our time here felt like home. Would and hope to come back again soon.
Bill T.
Stayed Mar 2024
Peace of mindOur Book with Confidence guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value