Holiday Homes in Southwest Coast Florida

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Find holiday rentals that suit your style

apart-hotel image
Aparthotels
Aparthotels
villa image
Villas
Villas

Check prices for these dates

Next weekend
13 Nov - 15 Nov
In two weeks
20 Nov - 22 Nov
In one month
4 Dec - 6 Dec
In two months
1 Jan - 3 Jan

Our top choices for Southwest Coast Florida holiday homes

A spacious living room with a grey sofa, striped armchair, and a woven coffee table. Large windows offer a view of a tropical garden.

1. Driftwood Inn

Driftwood Inn
4.0 star property
Mid Island
10.0 out of 10, Exceptional, (11 reviews)
"Great place to stay on sanibel"
United States
Terri
The price is AU$653
includes taxes & fees
8 Nov - 9 Nov
Driftwood Inn
A modern living room with a dining area, a grey sofa, a coffee table, and a wall clock.

2. Lakeside Oasis

Lakeside Oasis
2.0 star property
Iona
The price is AU$355
includes taxes & fees
9 Nov - 10 Nov
Lakeside Oasis
A bedroom with a large bed, a ceiling fan, a dresser, and a balcony with a view of palm trees.

3. coastal chic cottage "Heron" minutes to the beach! JULY SAVINGS!

coastal chic cottage "Heron" minutes to the beach! JULY SAVINGS!
West End
9.2 out of 10, Wonderful, (45 reviews)
"This was my second stay . It’s so amazing and the location is perfect !!!! We will be back !"
United States
EMILY B.
The price is AU$630
includes taxes & fees
10 Nov - 11 Nov
coastal chic cottage "Heron" minutes to the beach! JULY SAVINGS!
A kitchen with a large island, white cabinets, a black door, and teal bar stools.

4. BEACHSIDE COZY GETAWAY! Walk/Bike to Beach,Dining,Bars,Small fenced yard for pet

BEACHSIDE COZY GETAWAY! Walk/Bike to Beach,Dining,Bars,Small fenced yard for pet
Naples Park
8.8 out of 10, Excellent, (36 reviews)
"Perfect location for a person traveling for work . Hospital , Beach and Mercato all under a mile away . Got to enjoy Beautiful sunsets and take a few bicycles rides when not working . Bed was comfortable and having a washer dryer was helpful . Would stay again"
United States
Anonymous traveller
The price is AU$455
includes taxes & fees
15 Nov - 16 Nov
BEACHSIDE COZY GETAWAY! Walk/Bike to Beach,Dining,Bars,Small fenced yard for pet
A modern kitchen with white cabinets, a granite countertop, a built-in oven, and a microwave.

5. Noel Real Estate

Noel Real Estate
2.0 star property
East Naples
9.0 out of 10, Wonderful, (4 reviews)
"Property was easy to find and just as described and listed. very home-feeling and comfortable. "
United States
Lauren
The price is AU$571
includes taxes & fees
6 Dec - 7 Dec
Noel Real Estate
A living room with a sofa, two armchairs, a coffee table, a bookshelf, and a guitar.

6. Old Floridian cottage in Historic Gulf Village

Old Floridian cottage in Historic Gulf Village
Olde Englewood Village
9.8 out of 10, Exceptional, (61 reviews)
"Very good, great location 👍👍"
United States
James M.
The price is AU$382
includes taxes & fees
1 Dec - 2 Dec
Old Floridian cottage in Historic Gulf Village
A multi-level house with a white exterior, a staircase, and a deck area.

7. North Captiva Steps to Gulf Beaches Last Minute Offers Beach + Golf Cart + Club

North Captiva Steps to Gulf Beaches Last Minute Offers Beach + Golf Cart + Club
North Captiva Island
10.0 out of 10, Exceptional, (37 reviews)
"Amazing stay!Beds were comfortable, kitchen was well stocked. We would stay here again and again. "
United States
Tanya J.
The price is AU$1,340
includes taxes & fees
9 Nov - 10 Nov
North Captiva Steps to Gulf Beaches Last Minute Offers Beach + Golf Cart + Club
An indoor swimming pool with a glass ceiling, a lounge area with chairs and a table, and a view of the outside.

8. Lakeview Suite with Pool — Minutes to Downtown Naples & Beautiful Beaches

Lakeview Suite with Pool — Minutes to Downtown Naples & Beautiful Beaches
East Naples
9.2 out of 10, Wonderful, (56 reviews)
"We had a great visit. Quiet and well kept."
United States
Andrew F.
The price is AU$464
includes taxes & fees
22 Nov - 23 Nov
Lakeview Suite with Pool — Minutes to Downtown Naples & Beautiful Beaches
A pool area with a covered patio, chairs, and a ceiling fan.

9. Charming Beach Cottage with private pool - only 2 miles to stunning Bonita Beach

Charming Beach Cottage with private pool - only 2 miles to stunning Bonita Beach
Bonita Shores
10.0 out of 10, Exceptional, (203 reviews)
"Great place to stay"
United States
Joshua D.
The price is AU$600
includes taxes & fees
8 Nov - 9 Nov
Charming Beach Cottage with private pool - only 2 miles to stunning Bonita Beach
A modern kitchen with a central island, wooden cabinets, and a built-in oven.

10. NEW!! The “WATERSIDE” COTTAGE~With dockage

NEW!! The “WATERSIDE” COTTAGE~With dockage
Bokeelia
10.0 out of 10, Exceptional, (52 reviews)
"We had a great stay, was exactly as described. The host had great communication and gave great advice for the property and surrounding area."
United States
Jennifer D.
The price is AU$632
includes taxes & fees
8 Nov - 9 Nov
NEW!! The “WATERSIDE” COTTAGE~With dockage
A modern kitchen with a central island, stainless steel appliances, and a ceiling fan.

11. Dreams Away - Sleeps 10 Pool Golf Fun

Dreams Away - Sleeps 10 Pool Golf Fun
2.0 star property
Oakland Hills
The price is AU$519
includes taxes & fees
9 Nov - 10 Nov
Dreams Away - Sleeps 10 Pool Golf Fun
A spacious living room with a fireplace, a large TV mounted on a stone wall, a modern chandelier, and a kitchen area with a marble countertop.

12. Beach Bliss~Walk to Beach & Times Square~Private Pool

Beach Bliss~Walk to Beach & Times Square~Private Pool
Fort Myers Beach
9.8 out of 10, Exceptional, (25 reviews)
"Perfect location, great long weekend with friends."
United States
Jennifer B.
The price is AU$641
includes taxes & fees
18 Nov - 19 Nov
Beach Bliss~Walk to Beach & Times Square~Private Pool
A spacious living room with a beige sofa, a glass coffee table, and a ceiling fan.

13. Completely remodeled beautiful waterfront property on canal with dock

Completely remodeled beautiful waterfront property on canal with dock
Port Charlotte
9.6 out of 10, Exceptional, (74 reviews)
"Beautiful place to stay, great location.The decor and style of this home is absolutely gorgeous. Communication was top-notch. Would absolutely stay here again."
United States
Gale F.
The price is AU$353
includes taxes & fees
15 Nov - 16 Nov
Completely remodeled beautiful waterfront property on canal with dock
A swimming pool with a hot tub area, surrounded by a glass enclosure, and palm trees in the background.

14. The Dolphin

The Dolphin
Nokomis
9.8 out of 10, Exceptional, (21 reviews)
"The cottage was comfortable and the pool was relaxing. "
United States
daniel
The price is AU$329
includes taxes & fees
8 Nov - 9 Nov
The Dolphin
A modern kitchen with a bar area, a dining table, and a sofa in a living room.

15. Mimosa Memories

Mimosa Memories
South Venice
9.6 out of 10, Exceptional, (41 reviews)
"Clean"
United States
Hector G.
Mimosa Memories
A modern kitchen with a central island, bar stools, a window, and a dark cabinet.

16. Secluded Cottage with Hot Tub, Walking Distance to Benderson and UTC.

Secluded Cottage with Hot Tub, Walking Distance to Benderson and UTC.
The Meadows
10.0 out of 10, Exceptional, (29 reviews)
"The perfect place and the best rental I’ve stayed in!! All the descriptions are perfect. If you’re looking for a private getaway that’s close and cozy, this is it."
United States
Emma
The price is AU$349
includes taxes & fees
10 Nov - 11 Nov
Secluded Cottage with Hot Tub, Walking Distance to Benderson and UTC.
A wooden beach pavilion with a checkered roof and open sides, overlooking the beach.

17. Anna Maria Beach Condo 1/1

Anna Maria Beach Condo 1/1
Bradenton Beach
9.8 out of 10, Exceptional, (239 reviews)
"Great place to stay!"
United States
Donna B.
The price is AU$523
includes taxes & fees
8 Nov - 9 Nov
Anna Maria Beach Condo 1/1
A vase with dried plants on a wooden table, a decorative metal piece on the wall, and a small green bottle beside the vase.

18. Centrally located! 6 miles to Siesta and St. Armands. 2 miles to downtown.

Centrally located! 6 miles to Siesta and St. Armands. 2 miles to downtown.
Southgate
10.0 out of 10, Exceptional, (84 reviews)
"The place was super cute, clean, quiet, cozy, and in a great location. The host was very communicative and sweet. Definitely a great stay, 10/10 recommend!"
United States
Sierra B.
The price is AU$386
includes taxes & fees
8 Nov - 9 Nov
Centrally located! 6 miles to Siesta and St. Armands. 2 miles to downtown.
A dining area with a round wooden table, chairs, a coffee machine, a refrigerator, and a window with blinds.

19. Nautical Nook

Nautical Nook
Englewood
9.8 out of 10, Exceptional, (16 reviews)
"It was super clean and the host was great"
United States
Dolores
The price is AU$349
includes taxes & fees
7 Nov - 8 Nov
Nautical Nook
A modern bedroom with a bed, a bedside table, a round dining table with chairs, and a large window with curtains.

20. [escape to paradise] siesta key beach getaway

[escape to paradise] siesta key beach getaway
Siesta Key
9.8 out of 10, Exceptional, (34 reviews)
"Very clean and great location! Beds very comfortable and owner very responsive and accommodating! Highly recommend staying here!"
United States
Tim T.
The price is AU$411
includes taxes & fees
8 Nov - 9 Nov
[escape to paradise] siesta key beach getaway
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties

Learn more about Southwest Coast Florida

Amazing beaches, island views and top sights from Key West Express to Siesta Key Beach—discover Southwest Coast Florida, a destination also famous for its live music scene.

See all hotels in Southwest Coast Florida
A sunset over a beach with a pier and people walking on the sand.

Explore a world of travel with Expedia