Holiday Rentals in Southwest Florida

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Holiday Rentals in Southwest Florida

Outdoor pool
The Suites at Fishermen’s Village- 2 Bedroom Suites
3.0 star property
9.8 out of 10, Exceptional, (541)
"Our stay was perfect. We will definitely stay here again "
The price is €164
per night
23 May - 24 May
The Suites at Fishermen’s Village- 2 Bedroom Suites
Beach/ocean view
Edison Beach House
3.5 star property
9.4 out of 10, Exceptional, (1074)
"Bedding fit on the bed the first night that we stayed. We went out for the day and found the bed was made despite that sign that says it will be done on the 3rd day of our stay. When they changed the bedding the sheets did not fit on the beds and the blanket kept sliding on the floor. The sliding doors need to be WD-40’d. They are very difficult to open and the room above our room sounded like they were moving a piano until 2 am. Between the doors and moving the patio furniture we hardly slept....
The price is €231
per night
22 May - 23 May
Edison Beach House
Lobby
Bellasera Resort
4.0 star property
9.6 out of 10, Exceptional, (1924)
"beautiful single bedroom unit that had everything we needed for an easy enjoyable stay. crib for baby was clean and prepared nicely. on-site restaurant was wonderful as well. not a far walk from downtown and near where everything interesting is."
The price is €294
per night
2 Jun - 3 Jun
Bellasera Resort
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Outdoor pool, a heated pool, open 7:00 AM to 8:00 PM, pool loungers
Hibiscus Suites - Gateway to Siesta Key
2.5 star property
8.6 out of 10, Excellent, (1995)
"We ended up staying here because the hotel we originally booked, sent us an email the day before we were leaving to tell us their pool would be undergoing maintenance while we were there (and the only place we wanted to be). We're so glad that happened because we loved the Hibiscus Suites! It exceeded any expectation we may have had. Russ and the rest of the staff was super friendly and accomodating, the rooms were BIG and completely updated, with a small kitchen, and living room, which we were...
The price is €141
per night
27 May - 28 May
Hibiscus Suites - Gateway to Siesta Key
Standard Studio | Private kitchen
Wiggins Pass Chalet
4.0 star property
9.6 out of 10, Exceptional, (129)
"Check in progress was easy and receptionist was incredibly kind! "
The price is €155
per night
28 May - 29 May
Wiggins Pass Chalet
Lobby
Hyatt Vacation Club at Coconut Cove, Bonita Springs
4.0 star property
9.2 out of 10, Wonderful, (403)
"The property is nice. Staff at front desk need to improve their servicd"
The price is €281
per night
27 May - 28 May
Hyatt Vacation Club at Coconut Cove, Bonita Springs
Cabin (Tiny House - Yellow Lifeguard Stand) | Living area
Tiny House Siesta
2.0 star property
8.4 out of 10, Very good, (130)
"Came to siesta keys for the first time, really enjoyed our time there and it was a beautiful tiny place"
The price is €164
per night
27 May - 28 May
Tiny House Siesta
Exterior
Kon Tiki Inn
2.0 star property
10.0 out of 10, Exceptional, (110)
"Amazing pool, like a dream."
The price is €137
per night
3 Jun - 4 Jun
Kon Tiki Inn
Grand Studio Suite, Kitchenette | Living area
Lazy Cuckoo Inn
3.5 star property
8.8 out of 10, Excellent, (124)
"Our place was spacious, clean and very well supplied. Highly recommend this place. It was better and more convenient than high priced rooms. Exceptionally pleased. Great value."
Lazy Cuckoo Inn
Beach nearby, white sand, beach towels
Marco Beach Vacation Suites
3.5 star property
8.0 out of 10, Very good, (709)
"Ok very good access to beach no food recommendations "
Marco Beach Vacation Suites
Balcony view
Lovers Key Resort
3.0 star property
8.8 out of 10, Excellent, (929)
"This was our 2nd time staying and will definitely come back again next year. I love it . The front desk name of Rae was wonderful & friendly. "
The price is €298
per night
22 May - 23 May
Lovers Key Resort
Outdoor pool
GullWing Beach Resort
3.5 star property
9.6 out of 10, Exceptional, (869)
"It's basically a condo you're staying in with all the amenities of home."
GullWing Beach Resort
Beach nearby, beach umbrellas, beach towels
Tropical Villas of Venice Beach
3.5 star property
9.6 out of 10, Exceptional, (191)
"They were so accommodating at Tropical Villas. As part of your stay you had beach chairs, beach umbrella, cooler, coffee pods, sand sifter, beach towels (all in your villa). On-site you have access to use bicycles and washer n dryer at no extra charge. The Elite Villa we stayed in had direct access to the enclosed bug free pool. Our room was extremly clean and reminiscent of old school Florida cottage. The grounds were lush and they even had a sweet little wild brown bunny who wondered around...
Tropical Villas of Venice Beach
Outdoor pool, pool umbrellas, pool loungers
GreenLinks Golf Villas at Lely Resort
3.0 star property
9.4 out of 10, Exceptional, (485)
"…"
GreenLinks Golf Villas at Lely Resort
Beach
IMG MEMORIAL DAY & SUMMER DISCOUNTS! AMI White Sand Beaches/Pickle Ball/GOLF/FUN
10.0 out of 10, Exceptional, (6)
"The house is absolutely beautiful. 4 bedrooms, 3 bathrooms (2 ensuite), well stocked , very nice lanai, big backyard, gas grill, the owner came right away when there was a small issue - she is Very nice. I would highly recommend this house to anyone who wants a beautiful place to stay. Looking forward to staying there again."
The price is €566
per night
14 Jun - 15 Jun
IMG MEMORIAL DAY & SUMMER DISCOUNTS! AMI White Sand Beaches/Pickle Ball/GOLF/FUN
Beach nearby, beach towels
Charming 3 Bedroom 2 Bath Home with Pool Just 2 Minutes from Anna Maria Island
9.0 out of 10, Wonderful, (9)
"The house was very clean, very cute, and exactly as described. It was in a great location, not far from longboat key, Anna, Maria Island, and Bradenton. Beware, there is a ceramic blue parrot hanging in one of the trees around the pool, this caught me off guards several times and always made me laugh. I would totally stay here again."
Charming 3 Bedroom 2 Bath Home with Pool Just 2 Minutes from Anna Maria Island
Terrace/patio
Venice Beach Villas
3.0 star property
9.4 out of 10, Exceptional, (374)
"Convenient to beach and downtown. Friendly staff. "
Venice Beach Villas
Exterior
Beachfront Paradise w/ Totally PRIVATE BEACH ON THE WATERFRONT , Bring your dog
9.6 out of 10, Exceptional, (157)
"The location and views were incredible! It was so great being right on the beach and it was easy to walk everywhere. Unfortunately the house is a little tired, the refrigerator should be replaced as the door doesn’t close well, the shower head in the primary bathroom should be replaced and the pillows/mattresses need updating. Again, the location and views are stunning and we had the best time playing on the beach and in the water all day, but for the expensive cost per night, we were...
The price is €775
per night
2 Jun - 3 Jun
Beachfront Paradise w/ Totally PRIVATE BEACH ON THE WATERFRONT , Bring your dog
Villa, 2 Bedrooms, Balcony, Gulf View | Living area
Marriott's Crystal Shores
3.5 star property
9.2 out of 10, Wonderful, (202)
"Muy bueno "
The price is €878
per night
22 May - 23 May
Marriott's Crystal Shores
Exterior
Holiday Inn Club Vacations Sunset Cove Resort, an IHG Hotel
4.0 star property
9.8 out of 10, Exceptional, (215)
"Girls getaway celebrating a friend’s birthday. Outstanding experience, exceeded expectations in every way. Highly recommend! "
Holiday Inn Club Vacations Sunset Cove Resort, an IHG Hotel
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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.

Other types of properties in Southwest Florida you may be interested in

Lobby sitting area
Kompose Boutique Hotel
3.0 star property
9.0 out of 10, Wonderful, (3388)
"Super pretty and very comfortable "
The price is €88
per night
28 May - 29 May
Kompose Boutique Hotel
Outdoor pool, pool loungers
Hyatt Regency Sarasota
4.0 star property
8.0 out of 10, Very good, (1004)
"So beautiful and peaceful staff was very friendly."
The price is €141
per night
27 May - 28 May
Hyatt Regency Sarasota
Outdoor pool
The Westin Sarasota
4.0 star property
8.8 out of 10, Excellent, (1008)
"Friendly staff, fast easy check in. Spacious rooms."
The price is €158
per night
29 May - 30 May
The Westin Sarasota
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.

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, apart-hotels, 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 €137 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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