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In two weeks
28 Nov - 30 Nov
In two months
9 Jan - 11 Jan
In three months
6 Feb - 8 Feb
In four months
6 Mar - 8 Mar

Featured Villas in Southwest Florida

Fishing
Matlacha Tiny Village

Matlacha Tiny Village

3.0 star property
Matlacha
8.8 out of 10, Excellent, (265)
"Amazing spot. Love it. Quiet, and very suitable for us. The hosts are amazing; they will do anything in their power to accommodate your needs. Highly recommend it."
United States
Isabel
The price is NZ$362
includes taxes & fees
17 Nov - 18 Nov
Matlacha Tiny Village
Exterior
Flamingo's Nest at the Beach Shack. Just one block from the beach!

Flamingo's Nest at the Beach Shack. Just one block from the beach!

Manasota Key
10.0 out of 10, Exceptional, (39)
"We loved our visit to Manasota Key! The Beach Shack is a great location! We were one of the first guests to stay after hurricane Milton. The house is now in great condition. The public beach park was closed, but there is still beach access just one block away. We loved our kayak ride in the bay! We also loved being just a 10 minute walk to all of the restaurants/bars. We went to spring training baseball games on our non beach days. We saw lovely sunsets on the gulf side and a lovely sunrise on...
United States
Scott J.
The price is NZ$584
includes taxes & fees
15 Nov - 16 Nov
Flamingo's Nest at the Beach Shack. Just one block from the beach!
Outdoor pool
River Wilderness Waterfront Cabins

River Wilderness Waterfront Cabins

2.5 star property
Everglades City
8.6 out of 10, Excellent, (269)
"I would recommend this place for pure rest and relaxation "
United States
Shodo
The price is NZ$463
includes taxes & fees
12 Nov - 13 Nov
River Wilderness Waterfront Cabins
Property grounds
W Bradenton Country Club Estates, 2 bed, 2Bath 7miles to Beaches

W Bradenton Country Club Estates, 2 bed, 2Bath 7miles to Beaches

2.0 star property
Bradenton
9.2 out of 10, Wonderful, (11)
"Everything about the stay was terrific. Very clean and modernized home. Close to beaches restaurants and shopping. Highly recommend this home"
United States
Mike C.
The price is NZ$767
includes taxes & fees
13 Nov - 14 Nov
W Bradenton Country Club Estates, 2 bed, 2Bath 7miles to Beaches
Property grounds
Sunswept Villa 4-riverwalk/park front w/ pool, near AMI beaches - pet friendly!

Sunswept Villa 4-riverwalk/park front w/ pool, near AMI beaches - pet friendly!

Bradenton
10.0 out of 10, Exceptional, (30)
"This was a lovely oasis for a warm getaway from the cold. Beautifully decorated, had everything we needed to enjoy a 2 week stay."
United States
Christine M.
The price is NZ$608
includes taxes & fees
15 Nov - 16 Nov
Sunswept Villa 4-riverwalk/park front w/ pool, near AMI beaches - pet friendly!
Exterior
Vacay in Luxury! 2 mins to the Beach!

Vacay in Luxury! 2 mins to the Beach!

Holmes Beach
9.8 out of 10, Exceptional, (67)
"Cozy stay at this beautiful villa. Great customer service, was very fast to respond to questions we had. Highly recommend for a fun and comfortable stay. "
United States
Donald R.
The price is NZ$572
includes taxes & fees
18 Nov - 19 Nov
Vacay in Luxury! 2 mins to the Beach!
Terrace/patio
Water Front Boundary Vacation Home Villa close to beaches, golfing, Fishing

Water Front Boundary Vacation Home Villa close to beaches, golfing, Fishing

Oakland Hills
9.8 out of 10, Exceptional, (59)
"Perfect location for being close to Boca Grande and where we were fishing for the two days."
United States
Cindy M.
The price is NZ$575
includes taxes & fees
12 Nov - 13 Nov
Water Front Boundary Vacation Home Villa close to beaches, golfing, Fishing
Exterior
Cheerfull Villa.. Best Location in Naples!!! All you need in one home.

Cheerfull Villa.. Best Location in Naples!!! All you need in one home.

Naples
9.6 out of 10, Exceptional, (14)
"The house was perfect for our stay. Everything was nice and clean, access was very simple and everything we needed was right there!"
United States
brian b.
The price is NZ$833
includes taxes & fees
12 Nov - 13 Nov
Cheerfull Villa.. Best Location in Naples!!! All you need in one home.
Property grounds
Beautiful house with lake view

Beautiful house with lake view

Englewood East
10.0 out of 10, Exceptional, (10)
"Amazing beautiful place , very spacious , very easy to book. "
United States
Amara D.
The price is NZ$448
includes taxes & fees
12 Nov - 13 Nov
Beautiful house with lake view
Exterior
Updated Downtown Sarasota Villa, 2b/2b

Updated Downtown Sarasota Villa, 2b/2b

Central Sarasota
9.6 out of 10, Exceptional, (7)
"The outdoor grille was a pleasant surprise.One of the bathroom faucets was not functioning properly."
United States
David O.
The price is NZ$500
includes taxes & fees
12 Nov - 13 Nov
Updated Downtown Sarasota Villa, 2b/2b
Outdoor dining
Stunning Luxury villa "Sandpiper" across the street from the beach!

Stunning Luxury villa "Sandpiper" across the street from the beach!

East End
9.0 out of 10, Wonderful, (45)
"we enjoyed our stay at this lovely place"
Germany
Rolf E.
The price is NZ$909
includes taxes & fees
14 Nov - 15 Nov
Stunning Luxury villa "Sandpiper" across the street from the beach!
Exterior
Turtle Cay at The Beach Shack! Come On Down!

Turtle Cay at The Beach Shack! Come On Down!

Manasota Key
10.0 out of 10, Exceptional, (43)
"Everything was perfect! Check in, snacks provided,and all the little beach luxuries were there..definitely recommend and we will be back "
United States
alan s.
The price is NZ$585
includes taxes & fees
20 Nov - 21 Nov
Turtle Cay at The Beach Shack! Come On Down!
Outdoor dining
Sunny Fort Myers Retreat: Pet-Friendly near Downtown District, No Cleaning Fee!

Sunny Fort Myers Retreat: Pet-Friendly near Downtown District, No Cleaning Fee!

Dunbar
10.0 out of 10, Exceptional, (1)
"Communication with the host was so easy. She was very responsive to all messages and even gave us some recommendations for dining out. Extra nice touch of leaving some snacks and bottled water out. Plenty of towels and linens provided. Ample parking. Nice little patio to enjoy the beautiful weather. We definitely plan to be back!"
United States
Leesette B.
The price is NZ$339
includes taxes & fees
16 Nov - 17 Nov
Sunny Fort Myers Retreat: Pet-Friendly near Downtown District, No Cleaning Fee!
Exterior
Tranquil Tide Villa -Riverview w/pool on riverwalk, near AMI beach, pet friendly

Tranquil Tide Villa -Riverview w/pool on riverwalk, near AMI beach, pet friendly

Bradenton
9.8 out of 10, Exceptional, (20)
"Good Place to stay to enjoy area."
United States
DBCooper1996 T.
The price is NZ$622
includes taxes & fees
17 Nov - 18 Nov
Tranquil Tide Villa -Riverview w/pool on riverwalk, near AMI beach, pet friendly
Exterior
Beautiful Bungalow with Pool and Bay Views!

Beautiful Bungalow with Pool and Bay Views!

Anna Maria
9.8 out of 10, Exceptional, (37)
"Great location,great property,spacious,clean everything brand new in the property,beach across the street,my family love it!"
United States
Michel
The price is NZ$736
includes taxes & fees
2 Dec - 3 Dec
Beautiful Bungalow with Pool and Bay Views!
Outdoor pool, a heated pool
Relax with privacy! Villa in Bonita Springs! Modern, huge pool!

Relax with privacy! Villa in Bonita Springs! Modern, huge pool!

Bonita Springs
10.0 out of 10, Exceptional, (114)
"House was clean, and beds were comfortable. We mainly played in the pool. Nice location (close to center Bonita Springs). The artwork and sculptures were nice. Overall a good place to stay."
United States
Jamie W.
The price is NZ$1,096
includes taxes & fees
23 Nov - 24 Nov
Relax with privacy! Villa in Bonita Springs! Modern, huge pool!
Exterior
Beach Villa! Pool, Porch, and 2-Min Walk to Beach!

Beach Villa! Pool, Porch, and 2-Min Walk to Beach!

Holmes Beach
9.8 out of 10, Exceptional, (61)
"Place us espectacular , one block to a beautiful beach, nice and clean pool, place was clean "
United States
Enis
The price is NZ$685
includes taxes & fees
12 Nov - 13 Nov
Beach Villa! Pool, Porch, and 2-Min Walk to Beach!
Exterior
Mi Pequeña Casa - 2/2 on a lake

Mi Pequeña Casa - 2/2 on a lake

South Bradenton
The price is NZ$358
includes taxes & fees
18 Nov - 19 Nov
Mi Pequeña Casa - 2/2 on a lake
Terrace/patio
Seashell Shanty at The Beach Shack! Come On Down!

Seashell Shanty at The Beach Shack! Come On Down!

Manasota Key
10.0 out of 10, Exceptional, (43)
"We were attending a 60th family reunion. Many were staying down the beach near stump pass. We decided to check out off site bookings Everything was perfect. The gentleman even showed upbto jump one of our cars when we were checking out!"
United States
Joan S.
The price is NZ$584
includes taxes & fees
15 Nov - 16 Nov
Seashell Shanty at The Beach Shack! Come On Down!
Exterior
Waterview Vacation Retreat Close To Ocean

Waterview Vacation Retreat Close To Ocean

Oakland Hills
10.0 out of 10, Exceptional, (9)
"We've stayed in another property nearby owned by this host. This was another great stay. Beautiful home with lots of space and light. Love the fire pit out back at night. Easy driving to Spring Training games we were in town to see. Will definitely stay again. The host answers all communication quickly and the house is very clean and well appointed. "
United States
Kristi D.
The price is NZ$596
includes taxes & fees
12 Nov - 13 Nov
Waterview Vacation Retreat Close To Ocean
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
"The room was very clean and comfortable.. I would definitely stay hare again and recommend to any one."
Maritza 1-night trip
Posted 2 days ago
Compass by Margaritaville Hotel Naples

Find out more about Southwest Florida

Southwest Florida Villas information

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 Villas
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Frequently asked questions

How much do villas in Southwest Florida cost?
Prices for villas in Southwest Florida range between and per night. Whatever your budget, you'll find something that fits your needs on Expedia. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many villas are there in Southwest Florida?
Take your pick of villas in Southwest Florida. Whether you're getting away with the kids or your favourite friends, and wherever you're venturing, Expedia makes it a cinch to find the ideal space.
What is there to do near my villa in Southwest Florida?
The most important travel accessory for your Southwest Florida getaway is a fabulous itinerary! Henry B. Plant Museum, Orpheum Theatre and David A. Straz Jr. Centre for the Performing Arts are some of the top things to do if you're staying in Tampa. Sarasota also lures travellers with its superb attractions, such as Sarasota BayWalk. Want to explore more? Carve out some time for Ed Smith Stadium and Robert L. Taylor Community Complex too.

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