Search Holiday Rentals in Southwest Florida

Start date: Check-in selected.
To Date
End date: Check-out

  • 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

Check prices for these dates

In two weeks
16 Jan - 18 Jan
In two months
27 Feb - 1 Mar
In three months
27 Mar - 29 Mar
In four months
24 Apr - 26 Apr

Our top choices for Southwest Florida holiday rentals

Property grounds
Tropical Beach Resorts

Aparthotel in South Village

Tropical Beach Resorts
3.5 star property
9.4 out of 10, Exceptional, (5195)
"Great place to stay. Very nice getaway. "
United States
Joyeeta
The price is 3.776.271 ₫
4.861.296 ₫ total
includes taxes & fees
6 Jan - 7 Jan
Tropical Beach Resorts
Outdoor pool
The Suites at Fishermen’s Village- 2 Bedroom Suites

Condo resort in Punta Gorda Isles

The Suites at Fishermen’s Village- 2 Bedroom Suites
3.0 star property
9.8 out of 10, Exceptional, (1069)
"Excellent location and comfortable. Spacious rooms with full kitchens. "
United States
Janet
The price is 5.429.786 ₫
6.081.360 ₫ total
includes taxes & fees
10 Jan - 11 Jan
The Suites at Fishermen’s Village- 2 Bedroom Suites
Apartment, Multiple Beds, Partial Ocean View | Beach/ocean view
Edison Beach House

Aparthotel in Fort Myers Beach

Edison Beach House
3.5 star property
9.4 out of 10, Exceptional, (1603)
"Awesome stay "
United States
mary
The price is 4.365.122 ₫
5.746.444 ₫ total
includes taxes & fees
6 Jan - 7 Jan
Edison Beach House
Outdoor pool, a heated pool, open 7:00 AM to 8:00 PM, pool loungers
Hibiscus Suites - Gateway to Siesta Key

Aparthotel in Sarasota

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
8.6 out of 10, Excellent, (2226)
"Very nice place !"
United States
Ivette
The price is 6.579.624 ₫
7.434.975 ₫ total
includes taxes & fees
1 Feb - 2 Feb
Hibiscus Suites - Gateway to Siesta Key
Property amenity
The Residences at Siesta Key Beach by Hyatt Vacation Club

Aparthotel in South Village

The Residences at Siesta Key Beach by Hyatt Vacation Club
3.5 star property
9.6 out of 10, Exceptional, (306)
"The rooms were perfect, and the staff was great. The location was perfect and peaceful"
United States
Marybeth
The price is 10.704.474 ₫
13.432.800 ₫ total
includes taxes & fees
5 Feb - 6 Feb
The Residences at Siesta Key Beach by Hyatt Vacation Club
Exterior
Pelican Post at Anna Maria Island Inn

Apartment in Bradenton Beach

Pelican Post at Anna Maria Island Inn
3.0 star property
9.2 out of 10, Wonderful, (336)
"Easy access to Bridge St... Walk quick to beach. Quiet pool nice ... They can definitely improve the Internet as that was spotty. "
United States
Marc
Pelican Post at Anna Maria Island Inn
Laptop workspace, blackout curtains, free WiFi, bed sheets
StudioRes Fort Myers Airport

Aparthotel in Fort Myers

StudioRes Fort Myers Airport
3.0 star property
9.2 out of 10, Wonderful, (23)
"Loved stay here!!! "
United States
Melissa
The price is 2.659.031 ₫
2.964.820 ₫ total
includes taxes & fees
11 Jan - 12 Jan
StudioRes Fort Myers Airport
Exercise/lap pool
Hyatt Vacation Club at Coconut Cove, Bonita Springs

Aparthotel in Bonita Springs

Hyatt Vacation Club at Coconut Cove, Bonita Springs
4.0 star property
9.2 out of 10, Wonderful, (748)
"Great property. "
United States
Jan Pontus
The price is 6.989.453 ₫
8.819.098 ₫ total
includes taxes & fees
12 Jan - 13 Jan
Hyatt Vacation Club at Coconut Cove, Bonita Springs
Exterior
Kon Tiki Inn

Aparthotel in Venice Island

Kon Tiki Inn
2.5 star property
10.0 out of 10, Exceptional, (249)
"Great place! "
United States
Michelle
The price is 6.917.687 ₫
7.816.986 ₫ total
includes taxes & fees
20 Jan - 21 Jan
Kon Tiki Inn
Outdoor pool
GullWing Beach Resort

Aparthotel in South Island

GullWing Beach Resort
3.5 star property
9.4 out of 10, Exceptional, (932)
"The view of the beach was spectacular. "
United States
Carol
The price is 6.151.392 ₫
16.275.559 ₫ total
includes taxes & fees
6 Jan - 7 Jan
GullWing Beach Resort
Luxury Suite, Sea View | Beach/ocean view
Island Inn

Aparthotel in West End

Island Inn
3.5 star property
9.4 out of 10, Exceptional, (1124)
"Really nice, updated, and clean room with a screened waterfront balcony in a perfect place on the island (far enough away from the big resorts to be in a quieter area, but close enough to the center area of the island to be convenient). "
United States
Chris
The price is 7.597.232 ₫
8.471.045 ₫ total
includes taxes & fees
11 Jan - 12 Jan
Island Inn
Balcony view
Lovers Key Resort

Aparthotel in Fort Myers Beach

Lovers Key Resort
3.0 star property
8.8 out of 10, Excellent, (1020)
"The condo was great. Beautiful location and wonderful room."
United States
Jason
Lovers Key Resort
Exterior
Matlacha Tiny Village

Villa in Matlacha

Matlacha Tiny Village
3.0 star property
8.8 out of 10, Excellent, (270)
"Super clean! Super cute and easy for two. It is close to the road so we hear traffic, but the white noise helped with that. Communication was flawless! Would stay again. "
United States
Rhonda
The price is 3.123.014 ₫
5.453.708 ₫ total
includes taxes & fees
10 Jan - 11 Jan
Matlacha Tiny Village
On the beach, white sand
A Beach Retreat

Condo in Casey Key

A Beach Retreat
2.5 star property
9.2 out of 10, Wonderful, (583)
"Great location, recent updates"
United States
Michael
A Beach Retreat
Outdoor pool, a heated pool, open 8:00 AM to 8:00 PM, pool umbrellas
The Inn On Siesta Key

Cottage in Siesta Key

The Inn On Siesta Key
3.5 star property
10.0 out of 10, Exceptional, (192)
"Great place to stay! "
United States
Carlos
The Inn On Siesta Key
2 outdoor pools, pool cabanas (surcharge), pool umbrellas
Sundial Beach Resort & Spa

Condo resort in Mid Island

Sundial Beach Resort & Spa
5.0 star property
8.6 out of 10, Excellent, (2584)
"wonderful family friendly and spotless resort"
United States
Mary Anne
The price is 9.676.613 ₫
12.225.668 ₫ total
includes taxes & fees
6 Jan - 7 Jan
Sundial Beach Resort & Spa
Outdoor pool, pool umbrellas, pool loungers
Bridgewalk Resort

Aparthotel in Bridge Street

Bridgewalk Resort
3.5 star property
9.4 out of 10, Exceptional, (770)
"The staff was very courteous, friendly and helpful."
United States
Edward
The price is 6.719.213 ₫
7.592.711 ₫ total
includes taxes & fees
6 Jan - 7 Jan
Bridgewalk Resort
Beach
GreenLinks Golf Villas at Lely Resort

Aparthotel in Naples

GreenLinks Golf Villas at Lely Resort
3.0 star property
9.4 out of 10, Exceptional, (544)
"Clean and staff was helpful. Beautiful views"
United States
Rebecca
GreenLinks Golf Villas at Lely Resort
Deluxe Suite, 2 Bedrooms | Living area | TV
SeaSpray Resort

Aparthotel in Siesta Key

SeaSpray Resort
4.0 star property
9.4 out of 10, Exceptional, (84)
"Very clean very quiet and a great location to the beach."
United States
Dave
The price is 8.020.469 ₫
9.063.130 ₫ total
includes taxes & fees
6 Jan - 7 Jan
SeaSpray Resort
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
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Southwest Florida Hotel Reviews

Carlisle Inn

Carlisle Inn

10/10 Excellent
"Lovely hotel! So clean and comfortable. The free breakfast makes it even better. We highly recommend this hotel!"
Casey 3-night trip
Posted 6 hours ago
Carlisle Inn