A crowded beach with people sunbathing and swimming.

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Check prices for these dates

In two weeks
Sep 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four months
Jan 1 - Jan 3

Our top choices for Southwest Florida condo rentals

A balcony with a view of a marina, including boats and a dock with a boat.

1. Lovers Key Resort 803 Stunning views of Estero Bay

Lovers Key Resort 803 Stunning views of Estero Bay
Fort Myers Beach
10.0 out of 10, Exceptional, (63 reviews)
"It had everything we needed & more! Views were amazing!!! We saw dolphins, loved the restaurant, and the pool!"
United States
Rose D.
The price is ￥18,174
￥48,862 total
includes taxes & fees
Sep 9 - Sep 10
Lovers Key Resort 803 Stunning views of Estero Bay
A beach with clear skies, palm trees, and calm waves.

2. Resort style vacation, 2BR/2BA condo in the heart of Naples: 8min to the beach

Resort style vacation, 2BR/2BA condo in the heart of Naples: 8min to the beach
Central Naples
10.0 out of 10, Exceptional, (31 reviews)
"Host was very helpful, responded promptly to all communication and we will stay there again."
United States
Rick B.
The price is ￥14,567
￥57,105 total
includes taxes & fees
Sep 10 - Sep 11
Resort style vacation, 2BR/2BA condo in the heart of Naples: 8min to the beach
A modern hotel room with a large bed, a chandelier, a balcony with a view of the sea, and a sliding glass door.

3. SEASIDE 204. Luna Sea is a luxurious BEACHFRONT 2BR / 2BA Condo in FMB

SEASIDE 204. Luna Sea is a luxurious BEACHFRONT 2BR / 2BA Condo in FMB
Mid Island
10.0 out of 10, Exceptional, (148 reviews)
"Easy beach access. Quieter part of Ft Myers Beach, it was never overly crowded."
United States
Steven M.
The price is ￥26,976
￥81,064 total
includes taxes & fees
Sep 18 - Sep 19
SEASIDE 204. Luna Sea is a luxurious BEACHFRONT 2BR / 2BA Condo in FMB
A large orange armchair against a white wall with a 'Captiva' sign. There are two potted plants beside the chair.

4. Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,304 reviews)
"Clean room, beach access, easy parking, friendly staff"
United States
Karla
The price is ￥22,793
￥28,369 total
includes taxes & fees
Sep 10 - Sep 11
Captiva Beach Resort
An aerial view of a coastal town with beachfront properties, a marina, and clear blue waters.

5. Chadwick Cove Resort & Marina

Chadwick Cove Resort & Marina
4.0 star property
Manasota Key
9.2 out of 10, Wonderful, (26 reviews)
"Nic place to stay and enjoy the area"
United States
isabel
The price is ￥23,044
￥95,177 total
includes taxes & fees
Sep 17 - Sep 18
Chadwick Cove Resort & Marina
A bedroom with a large bed, a chandelier, a TV, and a view of the ocean.

6. SEASIDE 408. Sea La Vie is a luxurious BEACHFRONT 2BR / 2BA Condo in FMB

SEASIDE 408. Sea La Vie is a luxurious BEACHFRONT 2BR / 2BA Condo in FMB
Mid Island
10.0 out of 10, Exceptional, (143 reviews)
"Everything was great!! The place was very luxurious, clean, and with beautiful beach views. Also nice having the Publix across the street too!"
United States
Duane M.
SEASIDE 408. Sea La Vie is a luxurious BEACHFRONT 2BR / 2BA Condo in FMB
A living room with a view of the ocean, a ceiling fan, and a wooden coffee table.

7. A Beach Retreat

A Beach Retreat
2.5 star property
Casey Key
9.2 out of 10, Wonderful, (675 reviews)
"Great stay!!"
United States
Genghis
The price is ￥28,405
￥32,098 total
includes taxes & fees
Sep 20 - Sep 21
A Beach Retreat
An aerial view of a beach with a pier extending into the ocean, surrounded by buildings and greenery.

8. Olde Naples beautiful Condo Steps to Pier, Beach, Sunsets and restaurants!

Olde Naples beautiful Condo Steps to Pier, Beach, Sunsets and restaurants!
Old Naples
10.0 out of 10, Exceptional, (44 reviews)
"We had a great time! The location was amazing…a few steps to the beach and a few to downtown in the other direction. The place and beds were comfortable and it was well-stocked! Will come again!"
United States
Sheila N.
The price is ￥33,158
￥89,688 total
includes taxes & fees
Sep 9 - Sep 10
Olde Naples beautiful Condo Steps to Pier, Beach, Sunsets and restaurants!
A beach with a variety of seashells and a view of the ocean with waves.

9. Pet Friendly, Nightly CONDO! In-Unit Laundry, WiFi & Beach Gear; Walk to Dining/Shops (1 of 2 units)

Pet Friendly, Nightly CONDO! In-Unit Laundry, WiFi & Beach Gear; Walk to Dining/Shops (1 of 2 units)
Marco Island
9.6 out of 10, Exceptional, (87 reviews)
"Locate close to great restaurants and shoppers"
United States
terry J.
The price is ￥14,917
￥65,069 total
includes taxes & fees
Sep 14 - Sep 15
Pet Friendly, Nightly CONDO! In-Unit Laundry, WiFi & Beach Gear; Walk to Dining/Shops (1 of 2 units)
A water slide in a pool area with a rocky backdrop and a small waterfall.

10. Cedar Run Resort - Roam Hospitality

Cedar Run Resort - Roam Hospitality
3.5 star property
South Bradenton
9.4 out of 10, Exceptional, (8 reviews)
"I would stay again, very accommodating"
United States
Deliondra
The price is ￥21,504
￥68,371 total
includes taxes & fees
Sep 17 - Sep 18
Cedar Run Resort - Roam Hospitality
A lifeguard tower on a beach with clear blue water and a palm tree in the foreground.

11. Stunning Waterfront Condo By IMG & Anna Maria Island w/ Heated Pools & Hot Tubs

Stunning Waterfront Condo By IMG & Anna Maria Island w/ Heated Pools & Hot Tubs
Bradenton
9.8 out of 10, Exceptional, (124 reviews)
"We have stayed in Ervin's properties before and they are always extremely clean and updated to a high standard. We would definitely stay at this, or Ervin's other properties, in the future."
United States
Brian - Christine M.
The price is ￥15,723
￥46,932 total
includes taxes & fees
Sep 9 - Sep 10
Stunning Waterfront Condo By IMG & Anna Maria Island w/ Heated Pools & Hot Tubs
A wooden pathway leading to a beach with lush greenery and a clear sky.

12. Silver Sands 1BR – Gulfside Comfort #255 by RVA

Silver Sands 1BR – Gulfside Comfort #255 by RVA
Longboat Key
9.0 out of 10, Wonderful, (89 reviews)
"Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: What a great experience beautiful room,very clean,best location,private, very clean,all staff was polite and helpful"
United States
Anonymous traveler
The price is ￥28,980
￥59,087 total
includes taxes & fees
Sep 13 - Sep 14
Silver Sands 1BR – Gulfside Comfort #255 by RVA
A beach with clear turquoise water and a sandy shore.

13. Best views of the beach from your balcony Unit 301

Best views of the beach from your balcony Unit 301
Longboat Key
9.8 out of 10, Exceptional, (93 reviews)
"The location of the condo is 10 out of 10. The views and beach access cannot be beat. We enjoyed the space and appreciated the small but functional kitchen. We even found some beach supplies and an umbrella in the closet! This is a very great space and location. We will be back!"
United States
Anthony B.
Best views of the beach from your balcony Unit 301
A poolside table with a vase of flowers and two champagne flutes, overlooking a pool and palm trees.

14. 🛥️ 👀 Boat Watchers Paradise ☀️ w\ a Side of Dolphins🐬

🛥️ 👀 Boat Watchers Paradise ☀️ w\ a Side of Dolphins🐬
Olde Marco
9.8 out of 10, Exceptional, (56 reviews)
"Comfortable stay, quiet, very clean and nice view. Close to Publix and restaurants."
United States
Clelia
The price is ￥22,352
￥58,200 total
includes taxes & fees
Sep 9 - Sep 10
🛥️ 👀 Boat Watchers Paradise ☀️ w\ a Side of Dolphins🐬
A wooden pathway leading to a sandy beach with palm trees on either side.

15. Charming 2BR Condo By IMG Academy & Anna Maria Island w/ Heated Pools & Hot Tubs

Charming 2BR Condo By IMG Academy & Anna Maria Island w/ Heated Pools & Hot Tubs
Bradenton
9.8 out of 10, Exceptional, (161 reviews)
"Good location, good communication with host, very clean. Very easy check in and check out process "
United States
Cathleen R.
The price is ￥15,068
￥46,040 total
includes taxes & fees
Sep 9 - Sep 10
Charming 2BR Condo By IMG Academy & Anna Maria Island w/ Heated Pools & Hot Tubs
A beach with clear turquoise water and a sandy shore.

16. Beachfront Studio – Cabana #5B by RVA

Beachfront Studio – Cabana #5B by RVA
Longboat Key
8.2 out of 10, Very Good, (83 reviews)
"The cabana was a fantastic place to escape. It had easy access to both the beach and the pool. My kids loved every moment there."
United States
Roxana P.
The price is ￥22,658
￥47,717 total
includes taxes & fees
Sep 9 - Sep 10
Beachfront Studio – Cabana #5B by RVA
A wooden pathway leading to a beach with lush greenery on either side.

17. Oceanfront Bliss–Longboat Key Beach 106 by RVA

Oceanfront Bliss–Longboat Key Beach 106 by RVA
Longboat Key
8.8 out of 10, Excellent, (108 reviews)
"It was a great location. It had a nice pool area, plenty of beach chairs and beach goodies to use."
United States
Laurie L.
The price is ￥21,581
￥46,596 total
includes taxes & fees
Sep 10 - Sep 11
Oceanfront Bliss–Longboat Key Beach 106 by RVA
A modern kitchen with white cabinetry, a built-in dishwasher, and a large island with seating.

18. Beach Condo with Pool Near Holmes Beach!

Beach Condo with Pool Near Holmes Beach!
Holmes Beach
9.2 out of 10, Wonderful, (43 reviews)
"Everything was as expected and the location is great."
United States
Thomas T.
The price is ￥31,383
￥93,376 total
includes taxes & fees
Oct 1 - Oct 2
Beach Condo with Pool Near Holmes Beach!
A beach view from a balcony with a railing, ocean, and beach vegetation.

19. Sunny Days on LBK: Open Tomm, $125/nt + Fees!

Sunny Days on LBK: Open Tomm, $125/nt + Fees!
Longboat Key
10.0 out of 10, Exceptional, (97 reviews)
"Just got back from our long weekend trip to Longboat Key. Had a marvelous stay in the Vitamin Sea property. Everything was just perfect - really nice unit with all the necessities already stocked, steps from a beautiful beach and gorgeous sunsets, and great amenities (to include miniature golf)! Great pool for morning swims. Our host, Heidi, was a gem! Easy reservation/check-in and always making sure we had everything we needed. She even surprised us with a shell ornament gift and cinnamon...
United States
Richard
The price is ￥19,548
￥50,670 total
includes taxes & fees
Sep 9 - Sep 10
Sunny Days on LBK: Open Tomm, $125/nt + Fees!
An aerial view of a coastal resort with beachfront properties, a marina, and a marina with boats.

20. 3 Bedroom- Beachfront Condo with Beautiful Views of the Gulf

3 Bedroom- Beachfront Condo with Beautiful Views of the Gulf
Manasota Key
9.6 out of 10, Exceptional, (95 reviews)
"Great place and will definitely stay here again."
United States
Jessica S.
The price is ￥30,522
￥71,643 total
includes taxes & fees
Sep 13 - Sep 14
3 Bedroom- Beachfront Condo with Beautiful Views of the Gulf
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
"Tiene de todo para una juega estancia y diversión."
Elvis 3-night trip
Posted 2 hours ago
Compass by Margaritaville Hotel Naples

Find out more about Southwest Florida

Southwest Florida Condo Rentals information

Number of reviews
3,682
Accommodation
439 Condo Rentals
Lowest Price
￥28,369
Highest Price
￥569,076

Frequently asked questions

How much do condos in Southwest Florida cost?
Condos in Southwest Florida range from ￥28,369 to ￥569,076 per night. This gives you extra room for your whole family at a price that's easy on your wallet. 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.
What are the best condos in Southwest Florida?
Southwest Florida has multiple condos with a total average guest review rating of 9.2. Organizing an escape to Tampa? Look forward to a stay at New Two Bedroom Condo In Channelside Tam, a popular 3.5-star option with a terrace and a barbecue grill. Another highly rated choice is Channelside Condominiums. It has a 3.5-star rating and conveniences that include a swimming pool and individually decorated rooms.
How many condos are there in Southwest Florida?
Southwest Florida has 439 condos on offer. Enter your dates and destination and start planning your dream getaway today.
What are the best cheap condos in Southwest Florida?
With condos starting at just ￥28,369 per night, you'll have extra cash left over for exploring Southwest Florida. If Tampa is in your sights, check in to Nautical Watch Beach Resort. A tennis court and casino facilities help make this option a top choice. Expedia also has wallet-friendly condos in Sarasota. Get comfy at Captiva Beach Resort and enjoy conveniences such as a swimming pool and pillow top mattresses. Love to sightsee around Southwest Florida without hurting your hip pocket? Add some epic free attractions to your travel itinerary, such as Tampa Riverwalk in Tampa. Sarasota also has loads of things to do that don't cost a dime, including Siesta Key Beach. This price was 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.
Why book your condo in Southwest Florida with Expedia?
Reserving a condo in Southwest Florida is as easy as entering your travel dates and picking the option that meets your needs. On the lookout for something affordable or luxurious, or a property that also comes with a pool and free WiFi? Use Expedia's search filters to further narrow your search results and find the perfect fit.
How can I find cheap condos in Southwest Florida?
Expedia can help you search for cheap condos in Southwest Florida. To lock in a fantastic stay in a matter of clicks, try out the filter tool to refine your search results by budget, amenities and star rating.
What is there to do in Southwest Florida near my condo?
Whether you enjoy food, shopping, history or sightseeing, Southwest Florida promises something for everyone! The terrific city of Tampa has lots of attractions and activities, including Henry B. Plant Museum, Orpheum Theater and David A. Straz Jr. Center for the Performing Arts. If you're planning an escape to Sarasota, Sarasota BayWalk, Ed Smith Stadium and Robert L. Taylor Community Complex have to be on your itinerary.

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