Holiday Homes in Southwest Coast Florida

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Check prices for these dates

Next weekend
20 Nov - 22 Nov
In two weeks
27 Nov - 29 Nov
In one month
11 Dec - 13 Dec
In two months
8 Jan - 10 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 €414
includes taxes & fees
15 Nov - 16 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 €227
includes taxes & fees
15 Nov - 16 Nov
Lakeside Oasis
A kitchen with a large island, white cabinets, a black door, and teal bar stools.

3. 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 €330
includes taxes & fees
30 Nov - 1 Dec
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.

4. 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 €379
includes taxes & fees
16 Nov - 17 Nov
Noel Real Estate
A beach with a single seashell in the foreground and two people in the background.

5. 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 €567
includes taxes & fees
25 Nov - 26 Nov
coastal chic cottage "Heron" minutes to the beach! JULY SAVINGS!
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.

6. 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, (28 reviews)
"Perfect location, great long weekend with friends."
United States
Jennifer B.
The price is €369
includes taxes & fees
15 Nov - 16 Nov
Beach Bliss~Walk to Beach & Times Square~Private Pool
An indoor swimming pool with a glass ceiling, a lounge area with chairs and a table, and a view of the outside.

7. 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 €300
includes taxes & fees
22 Nov - 23 Nov
Lakeview Suite with Pool — Minutes to Downtown Naples & Beautiful Beaches
A spacious living room with a beige sofa, a glass coffee table, and a ceiling fan.

8. 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 €228
includes taxes & fees
17 Nov - 18 Nov
Completely remodeled beautiful waterfront property on canal with dock
An aerial view of a coastal area with several small islands connected by bridges.

9. 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 €413
includes taxes & fees
15 Nov - 16 Nov
NEW!! The “WATERSIDE” COTTAGE~With dockage
A pool area with a covered patio, chairs, and a ceiling fan.

10. 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, (204 reviews)
"Great place to stay"
United States
Joshua D.
The price is €420
includes taxes & fees
22 Nov - 23 Nov
Charming Beach Cottage with private pool - only 2 miles to stunning Bonita Beach
A wooden beach pavilion with a checkered roof and open sides, overlooking the beach.

11. 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 €332
includes taxes & fees
17 Nov - 18 Nov
Anna Maria Beach Condo 1/1
A kitchen with white cabinets, a granite countertop, stainless steel appliances, and a tiled backsplash.

12. 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 €270
includes taxes & fees
18 Nov - 19 Nov
Centrally located! 6 miles to Siesta and St. Armands. 2 miles to downtown.
A swimming pool with a hot tub area, surrounded by a glass enclosure, and palm trees in the background.

13. 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 €211
includes taxes & fees
15 Nov - 16 Nov
The Dolphin
A beach with footprints in the sand and a cloudy sky.

14. 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 €225
includes taxes & fees
15 Nov - 16 Nov
Nautical Nook
A modern kitchen with a central island, bar stools, a window, and a dark cabinet.

15. 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)
"This is a hidden gem. I love how tucked away and secluded it was and yet so close to shopping and restaurants. I will definitely stay here again when I’m needing a place in Sarasota"
United States
Todd A.
The price is €257
includes taxes & fees
16 Nov - 17 Nov
Secluded Cottage with Hot Tub, Walking Distance to Benderson and UTC.
A modern kitchen with grey cabinets, a wooden countertop, stainless steel appliances, and a tiled backsplash.

16. Path to Paradise.

Path to Paradise.
Olde Englewood Village
9.6 out of 10, Exceptional, (8 reviews)
"Great little spot!"
United States
Matthew
The price is €247
includes taxes & fees
15 Nov - 16 Nov
Path to Paradise.
A modern bedroom with a bed, a bedside table, a round dining table with chairs, and a large window with curtains.

17. [escape to paradise] siesta key beach getaway

[escape to paradise] siesta key beach getaway
Siesta Key
9.8 out of 10, Exceptional, (34 reviews)
"Clean and great location! Would stay again! "
United States
Laura W.
The price is €232
includes taxes & fees
15 Nov - 16 Nov
[escape to paradise] siesta key beach getaway
A dining area with a dark wooden table, four chairs, and a hanging lamp.

18. Lakeview Bradenton Rental Near Beaches & IMG

Lakeview Bradenton Rental Near Beaches & IMG
South Bradenton
9.8 out of 10, Exceptional, (6 reviews)
"Very clean and comfortable. "
United States
Dee F.
The price is €218
includes taxes & fees
15 Dec - 16 Dec
Lakeview Bradenton Rental Near Beaches & IMG
A beachside restaurant with a thatched roof, wooden tables, and chairs, overlooking a sandy beach and the ocean.

19. LAST MINUTE DEAL, Charming Elevated Duplex – Relaxing Beach Getaway Near Anna Maria Island- Bay access

LAST MINUTE DEAL, Charming Elevated Duplex – Relaxing Beach Getaway Near Anna Maria Island- Bay access
Sunny Shores
9.6 out of 10, Exceptional, (45 reviews)
"Superb value, quiet area, responsive owner, very nicely appointed; will definitely book again for next visit to Anna Maria Island!"
United States
Bryce W.
The price is €436
includes taxes & fees
15 Nov - 16 Nov
LAST MINUTE DEAL, Charming Elevated Duplex – Relaxing Beach Getaway Near Anna Maria Island- Bay access
A house with a porch, number 203, and a ceiling fan.

20. The Hideaways at Point Pleasant (Pine Side)

The Hideaways at Point Pleasant (Pine Side)
Bradenton
9.8 out of 10, Exceptional, (182 reviews)
"Great location and wonderful place to stay."
United States
Theresa H.
The price is €263
includes taxes & fees
15 Nov - 16 Nov
The Hideaways at Point Pleasant (Pine Side)
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.
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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.

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