A crowded beach with people sunbathing and swimming.

Search Southwest Florida Villa Rentals from CA $283

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Southwest Florida villas

A beachside area with colorful beach houses, a dock, and a sandy beach.

1. Matlacha Tiny Village

Matlacha Tiny Village
3.0 star property
Matlacha
8.8 out of 10, Excellent, (298 reviews)
"So cute and clean nice dock to sit and relax or fish. Kayaks available to use free as well with life jackets paddles, etc. well equipped rental we can’t wait to go again! Great communication with hosts."
United States
Lori
The price is CA $187
CA $315 total
includes taxes & fees
Oct 19 - Oct 20
Matlacha Tiny Village
A wooden deck with outdoor seating overlooking a lake, surrounded by dense greenery.

2. River Wilderness Waterfront Cabins

River Wilderness Waterfront Cabins
2.5 star property
Everglades City
8.6 out of 10, Excellent, (301 reviews)
"Staff was accommodating. Perfect setting and location. We are a repeat customer."
United States
Tangela
The price is CA $274
CA $313 total
includes taxes & fees
Oct 19 - Oct 20
River Wilderness Waterfront Cabins
A beach shack with a sign reading 'BEACH SHACK MANASOTA KEY,' a bicycle parked outside, and a chair and table set up for outdoor dining.

3. 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, (47 reviews)
"This was such a cute place to stay rhat is conveniently located via walking diatance to the beach and local restaurants. "
United States
Renay S.
The price is CA $238
CA $526 total
includes taxes & fees
Oct 19 - Oct 20
Turtle Cay at The Beach Shack! Come On Down!
A table with a tray containing a cookie and two cups, set in a covered outdoor area with a view of a lake and greenery.

4. Beautiful house with lake view

Beautiful house with lake view
Englewood East
9.6 out of 10, Exceptional, (17 reviews)
"Amazing beautiful place , very spacious , very easy to book. "
United States
Amara D.
The price is CA $140
CA $283 total
includes taxes & fees
Oct 19 - Oct 20
Beautiful house with lake view
Exterior

5. Stunning Luxury villa Sandpiper across the street from the beach!

Stunning Luxury villa Sandpiper across the street from the beach!
East End
8.8 out of 10, Excellent, (53 reviews)
"Excellent property, very clean, modern, centrally located, close to restaurants and beach. Absolutely pleasant."
United States
Fernando F.
The price is CA $226
CA $727 total
includes taxes & fees
Oct 19 - Oct 20
Stunning Luxury villa Sandpiper across the street from the beach!
An indoor swimming pool with a hot tub, surrounded by a glass enclosure with a view of a grassy yard and trees.

6. La Finca... Beautiful Countryside Home

La Finca... Beautiful Countryside Home
Naples
8.6 out of 10, Excellent, (12 reviews)
"Great communication and welcoming "
United States
Chris R.
The price is CA $170
CA $653 total
includes taxes & fees
Oct 19 - Oct 20
La Finca... Beautiful Countryside Home
An outdoor patio area with a seating arrangement, a hammock, and a view of a grassy yard and trees.

7. 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, (78 reviews)
"Great hosts and great stay! Would highly recommend."
United States
Kerry M.
The price is CA $151
CA $502 total
includes taxes & fees
Oct 19 - Oct 20
Water Front Boundary Vacation Home Villa close to beaches, golfing, Fishing
A residential property with a paved driveway leading to a garage, surrounded by palm trees and a well-maintained lawn.

8. Lake Marlin Villa 2

Lake Marlin Villa 2
Englewood East
10.0 out of 10, Exceptional, (20 reviews)
"House was very clean and the location was just what we were looking for. "
United States
Maria K.
The price is CA $165
CA $313 total
includes taxes & fees
Nov 18 - Nov 19
Lake Marlin Villa 2
A residential area with a pond, palm trees, and houses with sloped roofs.

9. Waterview Vacation Retreat Close To Ocean

Waterview Vacation Retreat Close To Ocean
Oakland Hills
10.0 out of 10, Exceptional, (19 reviews)
"The property was great for 3 adults on a golf trip."
United States
Lisa D.
The price is CA $144
CA $492 total
includes taxes & fees
Oct 19 - Oct 20
Waterview Vacation Retreat Close To Ocean
A dining area with a table and chairs, a green wall with a sign, and a view of palm trees and greenery.

10. Salty Lime Villa 2-Riverview w/pool on riverwalk, near AMI beaches, pet friendly

Salty Lime Villa 2-Riverview w/pool on riverwalk, near AMI beaches, pet friendly
Bradenton
10.0 out of 10, Exceptional, (40 reviews)
"Very nice place and quiet. Enjoyed the secluded pool and the variety of plants and flowers everywhere. The Riverwalk was nice too."
United States
Craig C.
The price is CA $181
CA $421 total
includes taxes & fees
Oct 19 - Oct 20
Salty Lime Villa 2-Riverview w/pool on riverwalk, near AMI beaches, pet friendly
A covered patio with a table and chairs, a stone floor, and a view of a residential street and greenery.

11. SPRING SPECIAL!!! 2/2 BEAUTIFUL VILLA! 2 BR, 2 BA, Heated pool and Jacuzzi! WiFi

SPRING SPECIAL!!! 2/2 BEAUTIFUL VILLA! 2 BR, 2 BA, Heated pool and Jacuzzi! WiFi
Sarasota
9.4 out of 10, Exceptional, (51 reviews)
"The condo is beautifully furnished and equipped with everything we needed. It was very comfortable and we would definitely stay there again."
United States
Sharon M.
The price is CA $204
CA $709 total
includes taxes & fees
Oct 19 - Oct 20
SPRING SPECIAL!!! 2/2 BEAUTIFUL VILLA! 2 BR, 2 BA, Heated pool and Jacuzzi! WiFi
A resort with a swimming pool, a covered patio, and a view of the ocean.

12. 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, (39 reviews)
"This was a great place to stay. Easy access to everything the area has to offer."
United States
Terri B.
The price is CA $181
CA $421 total
includes taxes & fees
Oct 19 - Oct 20
Sunswept Villa 4-riverwalk/park front w/ pool, near AMI beaches - pet friendly!
A serene lakeside setting with large trees and a white gazebo.

13. 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, (30 reviews)
"Beautiful property and lovely backyard. The Riverwalk was perfect for our 2 pups and the host was very quick to respond and very nice. Would definitely stay again."
United States
Kay S.
The price is CA $181
CA $421 total
includes taxes & fees
Oct 19 - Oct 20
Tranquil Tide Villa -Riverview w/pool on riverwalk, near AMI beach, pet friendly
A single-story house with a white exterior, a dark roof, and a front door.

14. Lakefront 2BR Bradenton Rental Near IMG & Beaches

Lakefront 2BR Bradenton Rental Near IMG & Beaches
South Bradenton
8.8 out of 10, Excellent, (3 reviews)
"Very clean. No tissues or napkins🤔. Recommend pump hand soap instead of little bars. Also, 2 outdoor chaises were ripped and 1 out of 2 outdoor chairs was broken and unable to use the.."
United States
Laura
The price is CA $138
CA $339 total
includes taxes & fees
Oct 27 - Oct 28
Lakefront 2BR Bradenton Rental Near IMG & Beaches
A bicycle parked outside a building with a 'Hello' mat at the entrance.

15. [Beach Elements] pool view withprivate beach access

[Beach Elements] pool view withprivate beach access
Siesta Key
9.6 out of 10, Exceptional, (44 reviews)
"The space was clean and well-equipped, and the host was easily reachable and responded quickly when I asked a question. The private beach access was nice. I would stay here again. "
United States
Natalie M.
The price is CA $162
CA $447 total
includes taxes & fees
Oct 26 - Oct 27
[Beach Elements] pool view withprivate beach access
A covered patio with a round table and chairs, a ceiling fan, and a view of a tropical garden.

16. The Driftwood Inn Cottages

The Driftwood Inn Cottages
Mid Island
10.0 out of 10, Exceptional, (1 review)
" An absolute gem in Sanibel!Our stay at the Driftwood Inn via VRBO was nothing short of wonderful. From the moment we arrived, we were impressed by how clean, comfortable, and well-maintained the property was. It has that perfect, relaxing Sanibel charm and provided everything we needed for a flawless vacation. The location was fantastic, making it easy to explore the island and enjoy the beaches. The hosts were excellent and made the entire process seamless. We truly loved our time here and...
United States
Cera - Tim A.
The price is CA $255
CA $612 total
includes taxes & fees
Oct 19 - Oct 20
The Driftwood Inn Cottages
A covered outdoor swimming pool with a view of a residential area.

17. Gulf access home, heated pool & kayaks

Gulf access home, heated pool & kayaks
Pelican
9.4 out of 10, Exceptional, (12 reviews)
"Perfect waterfront home, beautiful sunsets and sunrises. New favorite home."
United States
Brett B.
The price is CA $161
CA $668 total
includes taxes & fees
Oct 19 - Oct 20
Gulf access home, heated pool & kayaks
Pool

18. Private Pool, Game Room & Tiki Bar, Minutes to Englewood's Gulf Beaches

Private Pool, Game Room & Tiki Bar, Minutes to Englewood's Gulf Beaches
Englewood South
10.0 out of 10, Exceptional, (4 reviews)
"This was a wonderful vacation! The house was perfect! Very clean and decorated beautifully! We had everything that we needed! Great location too! We would recommend this house to anyone coming to Englewood, it was wonderful! We will be coming back! Thank you for sharing your beautiful house with us!!"
United States
Lisa M.
The price is CA $208
CA $630 total
includes taxes & fees
Oct 28 - Oct 29
Private Pool, Game Room & Tiki Bar, Minutes to Englewood's Gulf Beaches
A covered outdoor swimming pool with lounge chairs and string lights.

19. Sunset Lanai & Screened Pool · Waterfront Views

Sunset Lanai & Screened Pool · Waterfront Views
Caloosahatchee
10.0 out of 10, Exceptional, (5 reviews)
"Everything inside the house was brand new and clean and it was perfect for our family of four. We had our dog so the dog door going out to the pool area was absolutely huge. Great place!"
United States
Melissa R.
The price is CA $255
CA $939 total
includes taxes & fees
Oct 27 - Oct 28
Sunset Lanai & Screened Pool · Waterfront Views
A sunlit balcony with a round glass table and wicker chairs, overlooking a well-maintained lawn and a house in the background.

20. Bright Spacious Villa with a Pool – 15 min from Siesta Beach #1 Beach in the USA

Bright Spacious Villa with a Pool – 15 min from Siesta Beach #1 Beach in the USA
Sarasota
9.6 out of 10, Exceptional, (27 reviews)
"Excellent stay. Very clean and facilities were great "
United Kingdom
Jennie A.
The price is CA $214
CA $569 total
includes taxes & fees
Oct 19 - Oct 20
Bright Spacious Villa with a Pool – 15 min from Siesta Beach #1 Beach in the USA
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 Hotel by Margaritaville Anna Maria Sound

Compass Hotel by Margaritaville Anna Maria Sound

10/10 Excellent
"Breakfast was amazing and fresh !!"
Taylor 4-night trip
Posted 2 hours ago
Compass Hotel by Margaritaville Anna Maria Sound

Find out more about Southwest Florida

Southwest Florida Villas information

Number of reviews
698
Accommodation
55 Villas
Lowest Price
CA $283
Highest Price
CA $939

Frequently asked questions

How much do villas in Southwest Florida cost?
Prices for villas in Southwest Florida range between CA $283 and CA $939 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 55 villas in Southwest Florida. Whether you're getting away with the kids or your favorite friends, and wherever you're venturing, Expedia makes it a cinch to find the ideal space.
Why book your villa in Southwest Florida with Expedia?
We think arranging a vacation shouldn't be complicated, so if you're in search of villas at an affordable price, Expedia delivers. Stick to the budget and opt for an all-inclusive stay, or splurge on a 5-star villa to treat your sweetheart. Our handy filters make it easy to find a place in Southwest Florida that checks your boxes.
How can I find cheap villas in Southwest Florida?
Expedia is here to help you locate cheap villas in Southwest Florida. Use the filter tool to choose amenities, star rating and budget to refine your search and find the perfect stay in a matter of clicks.
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 Theater and David A. Straz Jr. Center for the Performing Arts are some of the top things to do if you're staying in Tampa. Sarasota also lures travelers 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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