A crowded beach with people sunbathing and swimming.

Southwest Florida Holiday Rentals

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Our top choices for Southwest Florida holiday rentals

Lovers Key Resort

Lovers Key Resort
3.0 star property
Fort Myers Beach
8.8 out of 10, Excellent, (1,065 reviews)
"Always a great stay"
United States
Jason
The price is NZ$504
includes taxes & fees
1 July - 2 July
Lovers Key Resort

Kon Tiki Inn

Kon Tiki Inn
2.5 star property
Venice Island
10.0 out of 10, Exceptional, (288 reviews)
"Great place to stay!!!"
United States
Tara
The price is NZ$220
includes taxes & fees
30 June - 1 July
Kon Tiki Inn

The Suites at Fishermen’s Village- 2 Bedroom Suites

The Suites at Fishermen’s Village- 2 Bedroom Suites
3.0 star property
Punta Gorda Isles
9.8 out of 10, Exceptional, (1,246 reviews)
"Great location clean and specious"
United States
Kathryn
The price is NZ$348
includes taxes & fees
30 July - 31 July
The Suites at Fishermen’s Village- 2 Bedroom Suites

Edison Beach House

Edison Beach House
3.5 star property
Fort Myers Beach
9.4 out of 10, Exceptional, (1,800 reviews)
"Every aspect fit our needs for this beach trip!"
United States
Lisa
The price is NZ$356
includes taxes & fees
2 July - 3 July
Edison Beach House

Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,272 reviews)
"Very clean rooms, excellent location and a very nice staff"
United States
Yanseli
The price is NZ$360
includes taxes & fees
7 July - 8 July
Captiva Beach Resort

Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (5,611 reviews)
"perfect stay and location for a family!"
United States
Jessica
The price is NZ$385
includes taxes & fees
1 July - 2 July
Tropical Beach Resorts

Island Inn

Island Inn
3.5 star property
West End
9.4 out of 10, Exceptional, (1,139 reviews)
"The place was amazing and the host was very gracious."
United States
Wendy
The price is NZ$532
includes taxes & fees
6 July - 7 July
Island Inn

GullWing Beach Resort

GullWing Beach Resort
3.5 star property
South Island
9.4 out of 10, Exceptional, (955 reviews)
"We really enjoyed our stay here and plan on staying here again!"
United States
Claudia
The price is NZ$907
includes taxes & fees
1 July - 2 July
GullWing Beach Resort

A Beach Retreat

A Beach Retreat
2.5 star property
Casey Key
9.2 out of 10, Wonderful, (644 reviews)
"Nice place ,clean and good location,quiet and relaxing."
United States
yohana
The price is NZ$407
includes taxes & fees
30 June - 1 July
A Beach Retreat

MALU LANI Inn & Marina

MALU LANI Inn & Marina
3.5 star property
Bokeelia
10.0 out of 10, Exceptional, (6 reviews)
"Overall, very friendly Gave me advice about the area Told me what live bands were playing that night Very fun definitely will be back"
United States
Kyle
The price is NZ$690
includes taxes & fees
6 July - 7 July
MALU LANI Inn & Marina

Noel Real Estate

Noel Real Estate
2.0 star property
East Naples
9.4 out of 10, Exceptional, (3 reviews)
"Property was easy to find and just as described and listed. very home-feeling and comfortable. "
United States
Lauren
The price is NZ$753
includes taxes & fees
11 July - 12 July
Noel Real Estate

Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
Sarasota
8.6 out of 10, Excellent, (2,352 reviews)
"great place to stay for a couple of nights. "
United States
Diana
The price is NZ$298
includes taxes & fees
30 June - 1 July
Hibiscus Suites - Gateway to Siesta Key

Pelican Post at Anna Maria Island Inn

Pelican Post at Anna Maria Island Inn
3.5 star property
Bradenton Beach
9.2 out of 10, Wonderful, (416 reviews)
"Great location - quiet, private, but just a few blocks from the beach, every eatery and nightlife option. Would definitely stay here again."
United States
Christopher
The price is NZ$450
includes taxes & fees
6 July - 7 July
Pelican Post at Anna Maria Island Inn

Sundial Beach Resort & Spa

Sundial Beach Resort & Spa
5.0 star property
Mid Island
8.6 out of 10, Excellent, (2,663 reviews)
"Excellent stay and amenities for families. "
United States
Megan
The price is NZ$945
includes taxes & fees
5 July - 6 July
Sundial Beach Resort & Spa

Bellasera Resort

Bellasera Resort
4.0 star property
Old Naples
9.6 out of 10, Exceptional, (2,286 reviews)
"Everything was great! Nice hotel."
United States
Yuliia
The price is NZ$553
includes taxes & fees
6 July - 7 July
Bellasera Resort

Home < 1-mi Walk to Warm Mineral Springs Park!

Home < 1-mi Walk to Warm Mineral Springs Park!
3.0 star property
North Port
The price is NZ$865
includes taxes & fees
30 June - 1 July
Home < 1-mi Walk to Warm Mineral Springs Park!

Cedar Run Resort - Roam Hospitality

Cedar Run Resort - Roam Hospitality
3.5 star property
South Bradenton
9.0 out of 10, Wonderful, (6 reviews)
"I would stay again, very accommodating"
United States
Deliondra
The price is NZ$1,110
includes taxes & fees
30 June - 1 July
Cedar Run Resort - Roam Hospitality

Bridgewalk Resort

Bridgewalk Resort
3.5 star property
Bridge Street
9.4 out of 10, Exceptional, (809 reviews)
"Centrally located, all the staff was excellent. Great place to stay! Will stay here again!"
United States
Keri
The price is NZ$643
includes taxes & fees
5 July - 6 July
Bridgewalk Resort

Emerald Entry Retreat

Emerald Entry Retreat
2.0 star property
LaBelle
The price is NZ$730
includes taxes & fees
2 July - 3 July
Emerald Entry Retreat

Secluded Cottage - Private BBQ Deck Firepit

Secluded Cottage - Private BBQ Deck Firepit
2.0 star property
Sarasota
Secluded Cottage - Private BBQ Deck Firepit
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

Find out more about Southwest Florida

Everything you need to know about Southwest Florida holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Southwest Florida holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Southwest Florida holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Southwest Florida holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Southwest Florida. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Southwest Florida holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Southwest Florida holiday rentals we have selected for you start as low as NZ$220 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Southwest Florida rentals

At Expedia, we put the best Southwest Florida holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Southwest Florida rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Southwest Florida holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Southwest Florida. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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