A crowded beach with people sunbathing and swimming.

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Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

Our top choices for Southwest Florida vacation homes

A modern living room with a dining area, a grey sofa, a coffee table, and a wall clock.

1. Lakeside Oasis

Lakeside Oasis
2.0 star property
Iona
Lakeside Oasis
A modern kitchen with white cabinets, a granite countertop, a built-in oven, and a microwave.

2. 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
Noel Real Estate
A spacious living room with a grey sofa, striped armchair, and a woven coffee table. Large windows offer a view of a tropical garden.

3. 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
Driftwood Inn
A spacious living room with a beige sofa, a glass coffee table, and a ceiling fan.

4. 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.
Completely remodeled beautiful waterfront property on canal with dock
A living room with a sofa, two armchairs, a coffee table, a bookshelf, and a guitar.

5. 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.
Old Floridian cottage in Historic Gulf Village
A modern living room with a large window, a flat-screen TV, and a potted plant.

6. Nestled in North Port. Updated 2 Bed / 1 Bath.

Nestled in North Port. Updated 2 Bed / 1 Bath.
North Port
10.0 out of 10, Exceptional, (25 reviews)
"Every part of this stay was perfect! "
United States
Stephen P.
Nestled in North Port. Updated 2 Bed / 1 Bath.
A modern kitchen with a central island, stainless steel appliances, and a ceiling fan.

7. Dreams Away - Sleeps 10 Pool Golf Fun

Dreams Away - Sleeps 10 Pool Golf Fun
2.0 star property
Oakland Hills
Dreams Away - Sleeps 10 Pool Golf Fun
A kitchen with a large island, white cabinets, a black door, and teal bar stools.

8. 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 traveler
BEACHSIDE COZY GETAWAY! Walk/Bike to Beach,Dining,Bars,Small fenced yard for pet
A bedroom with a large bed, a ceiling fan, a dresser, and a balcony with a view of palm trees.

9. 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.
coastal chic cottage "Heron" minutes to the beach! JULY SAVINGS!
A dining area with a dark wooden table, four chairs, and a hanging lamp.

10. 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.
Lakeview Bradenton Rental Near Beaches & IMG
A two-story house with a covered porch, a small front yard, and a clear blue sky.

11. The Hideaways at Point Pleasant (Palm Side)

The Hideaways at Point Pleasant (Palm Side)
Bradenton
10.0 out of 10, Exceptional, (177 reviews)
"Great downtown location! We enjoyed our stay!"
United States
Diane M.
The Hideaways at Point Pleasant (Palm Side)
A swimming pool with a hot tub area, surrounded by a glass enclosure, and palm trees in the background.

12. 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 Dolphin
A dining area with a round wooden table, chairs, a coffee machine, a refrigerator, and a window with blinds.

13. 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
Nautical Nook
A modern living room with a sofa, a blue armchair, and a wooden coffee table.

14. * * Endless Summer * * Beach, Unique & Comfort

* * Endless Summer * * Beach, Unique & Comfort
Naples Park
9.6 out of 10, Exceptional, (23 reviews)
"This is a great place with a great location! I was in Naples on business and this place made my 4 day stay a pleasant experience.I highly recommend staying here!"
United States
Mark B.
* * Endless Summer * * Beach, Unique & Comfort
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)
"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
Secluded Cottage with Hot Tub, Walking Distance to Benderson and UTC.
An indoor swimming pool with a glass ceiling, a lounge area with chairs and a table, and a view of the outside.

16. 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.
Lakeview Suite with Pool — Minutes to Downtown Naples & Beautiful Beaches
A house with a porch, number 203, and a ceiling fan.

17. 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 Hideaways at Point Pleasant (Pine Side)
A modern kitchen with grey cabinets, a wooden countertop, stainless steel appliances, and a tiled backsplash.

18. Path to Paradise.

Path to Paradise.
Olde Englewood Village
9.6 out of 10, Exceptional, (8 reviews)
"Great little spot!"
United States
Matthew
Path to Paradise.
A modern outdoor living space with a sofa, a hanging chair, and a coffee table.

19. "The Coastal Dream" only 3miles to the beach.

"The Coastal Dream" only 3miles to the beach.
East Naples
9.8 out of 10, Exceptional, (26 reviews)
"Great location, everything was perfect!"
United States
Jesse L.
"The Coastal Dream" only 3miles to the beach.
A multi-level house with a white exterior, a staircase, and a deck area.

20. 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.
North Captiva Steps to Gulf Beaches Last Minute Offers Beach + Golf Cart + Club
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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Top Southwest Florida Hotel Reviews

Compass by Margaritaville Hotel Naples

Compass by Margaritaville Hotel Naples

10/10 Excellent
"Best hotel breakfast ever.. real food Not powdered eggs or premade bacon.. Attention to detail keeping the joint immaculate..."
Edward 3-night trip
Posted 7 hours ago
Compass by Margaritaville Hotel Naples

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