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Flamingo Bay Holiday Rentals

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Our top choices for Flamingo Bay holiday rentals

1. Manatee Lookout Cottages - Boat to Beach, Dock, Pool, Kayaks, Direct Gulf Access

Manatee Lookout Cottages - Boat to Beach, Dock, Pool, Kayaks, Direct Gulf Access
Saint James City
10.0 out of 10, Exceptional, (3 reviews)
"The house was exactly as advertised. It was beautiful, clean, and easy to find. We really enjoyed our stay. 10/10 would recommend!"
United States
Bethany
The price is NZ$582
includes taxes & fees
14 Aug - 15 Aug
Manatee Lookout Cottages - Boat to Beach, Dock, Pool, Kayaks, Direct Gulf Access

2. Matlacha Tiny Village

Matlacha Tiny Village
3.0 star property
Matlacha
8.8 out of 10, Excellent, (295 reviews)
"We had a wonderful visit July 26th-28th. Check in was so easy. We stayed in the flamingo. The flamingo is so cute and charming. We had a wonderful time just relaxing and fishing off the dock with the grandkids. We love the kayaks. Tiny village is the perfect place for a little getaway and we can’t wait to book again."
United States
Heather
The price is NZ$337
includes taxes & fees
18 Aug - 19 Aug
Matlacha Tiny Village

3. Lazy Cuckoo Inn

Lazy Cuckoo Inn
2.0 star property
Fort Myers Beach
8.8 out of 10, Excellent, (296 reviews)
"Clean room, good location, easy check in instructions."
United States
Brooklyn
The price is NZ$161
includes taxes & fees
20 Aug - 21 Aug
Lazy Cuckoo Inn

4. Island Inn

Island Inn
3.5 star property
West End
9.4 out of 10, Exceptional, (1,145 reviews)
"Great views, clean room, amazing beach and staff!!! Can't wait to come."
United States
Daniel
The price is NZ$377
includes taxes & fees
7 Sept - 8 Sept
Island Inn

5. Bayside Villa 4224: Bright Corner Unit with Stunning Bay Views

Bayside Villa 4224: Bright Corner Unit with Stunning Bay Views
Captiva
8.8 out of 10, Excellent, (13 reviews)
"Highly recommend for families as this unit is located right by the pool and marina. Waterpark is within walking distance."
United States
DENISE H.
The price is NZ$786
includes taxes & fees
14 Aug - 15 Aug
Bayside Villa 4224: Bright Corner Unit with Stunning Bay Views

6. Bayside Villa 5110 | Upscale Bayfront Residence | In-unit laundry | Walk to the Beach

Bayside Villa 5110 | Upscale Bayfront Residence | In-unit laundry | Walk to the Beach
Captiva
9.6 out of 10, Exceptional, (23 reviews)
"Well kept condo."
United States
Joseph S.
The price is NZ$1,030
includes taxes & fees
14 Aug - 15 Aug
Bayside Villa 5110 | Upscale Bayfront Residence | In-unit laundry | Walk to the Beach

7. Modern Luxurious Condo, King Bed Suite, Waterfront + Pool, Near Downtown

Modern Luxurious Condo, King Bed Suite, Waterfront + Pool, Near Downtown
Caloosahatchee
9.2 out of 10, Wonderful, (40 reviews)
"Great stay here! Clean and spacious. Loved the amenities and the location ease of access."
United States
Brianna L.
The price is NZ$489
includes taxes & fees
27 Aug - 28 Aug
Modern Luxurious Condo, King Bed Suite, Waterfront + Pool, Near Downtown

8. Coastal Chic Cottage "Sandpiper" minutes to the beach! Free bikes

Coastal Chic Cottage "Sandpiper" minutes to the beach! Free bikes
West End
9.0 out of 10, Wonderful, (23 reviews)
"Loved our stay at the cottage. It was a perfect getaway for 2. Short walk to a quiet beach. Convenient to restaurants and Ding Darling.We will be back!"
United States
Catherine B.
The price is NZ$699
includes taxes & fees
14 Aug - 15 Aug
Coastal Chic Cottage "Sandpiper" minutes to the beach! Free bikes

9. Charming 1-bedroom apartment in Bokeelia with WiFi, AC, pool & heated spa

Charming 1-bedroom apartment in Bokeelia with WiFi, AC, pool & heated spa
Bokeelia
9.8 out of 10, Exceptional, (18 reviews)
"peaceful and quiet in a great place to getaway"
United States
Louis
The price is NZ$520
includes taxes & fees
25 Aug - 26 Aug
Charming 1-bedroom apartment in Bokeelia with WiFi, AC, pool & heated spa

10. Bayside Villa 4208 | Stunning Harbourview Residence| Walk to the Beach

Bayside Villa 4208 | Stunning Harbourview Residence| Walk to the Beach
Captiva
9.2 out of 10, Wonderful, (31 reviews)
"Very nice condo overlooking waterway. Nice pool and easy in and out. "
United States
William B.
The price is NZ$805
includes taxes & fees
15 Aug - 16 Aug
Bayside Villa 4208 | Stunning Harbourview Residence| Walk to the Beach

11. Cozy Luxury Suite In The Heart Of Fort Myers Close To Everything!

Cozy Luxury Suite In The Heart Of Fort Myers Close To Everything!
Daniels Corridor
9.4 out of 10, Exceptional, (64 reviews)
"Reasonable price and nicely kept suite with all the supplies."
United States
James g.
The price is NZ$288
includes taxes & fees
14 Aug - 15 Aug
Cozy Luxury Suite In The Heart Of Fort Myers Close To Everything!

12. Warm & Welcoming Rancher

Warm & Welcoming Rancher
Mariner
8.0 out of 10, Very good, (2 reviews)
"We needed a place to stay while in the area attending the annual vintage base ball conference and this place fot the bill."
United States
Tim P.
The price is NZ$588
includes taxes & fees
14 Aug - 15 Aug
Warm & Welcoming Rancher

13. Newly remodeled Parakeet cottage! Walking distance to beach, restaurants, shops!

Newly remodeled Parakeet cottage! Walking distance to beach, restaurants, shops!
East End
9.2 out of 10, Wonderful, (75 reviews)
"Great little place, really enjoyed having the kitchen and the grill. "
United States
Eric W.
The price is NZ$521
includes taxes & fees
11 Sept - 12 Sept
Newly remodeled Parakeet cottage! Walking distance to beach, restaurants, shops!

14. Captiva Villa 3213 | Chic Residence | Great Amenities | Walk to the Beach

Captiva Villa 3213 | Chic Residence | Great Amenities | Walk to the Beach
Captiva
9.0 out of 10, Wonderful, (19 reviews)
"We enjoyed our time here. No issues. "
United States
Rodney S.
The price is NZ$998
includes taxes & fees
14 Aug - 15 Aug
Captiva Villa 3213 | Chic Residence | Great Amenities | Walk to the Beach

15. SUNSHINE GETAWAY VACATION RENTALS

SUNSHINE GETAWAY VACATION RENTALS
Fort Myers
8.4 out of 10, Very good, (145 reviews)
"This is a beautiful place to stay and it is EXACTLY as pictured in the platform. No surprises and nothing left out. It was clean, space to eat and cook. Nice area to relax and private bedroom. Nice pool for swimming and the residents were pleasant. A great value! Thank you for accommodating us with last minute notice. Will recommend staying with you. "
United States
SUZANNE M.
The price is NZ$452
includes taxes & fees
30 Aug - 31 Aug
SUNSHINE GETAWAY VACATION RENTALS

16. Paradise Vacation Pool Home Last minute $155

Paradise Vacation Pool Home Last minute $155
Pelican
9.4 out of 10, Exceptional, (18 reviews)
"Beautiful place, great host ! Highly recommended ! "
United States
Titus C.
Paradise Vacation Pool Home Last minute $155

17. Newly remodeled Parrot Nest Toucan Cottage! Walk to beach, shops, restaurants!

Newly remodeled Parrot Nest Toucan Cottage! Walk to beach, shops, restaurants!
East End
9.6 out of 10, Exceptional, (54 reviews)
"Loved this place! So private and cute! We walked to Wickies for breakfast and lunch and did Mudbugs for dinner! Best beaches were Blind Pass and Tarpon Bay! Make sure to use the code for a discount for Adventures in Paradise Shelling tours!"
United States
Stephen
The price is NZ$521
includes taxes & fees
7 Sept - 8 Sept
Newly remodeled Parrot Nest Toucan Cottage! Walk to beach, shops, restaurants!

18. Edison Beach House

Edison Beach House
3.5 star property
Fort Myers Beach
9.4 out of 10, Exceptional, (1,868 reviews)
"Lovely stay. Right on a beautiful beach. Located near food, shopping etc. Great place to stay."
United States
Brian
The price is NZ$375
includes taxes & fees
16 Aug - 17 Aug
Edison Beach House

19. The Lovebird-sleeps 3! Great value on Sanibel-walk to dining, shops and Historic East End Lighthouse

The Lovebird-sleeps 3! Great value on Sanibel-walk to dining, shops and Historic East End Lighthouse
East End
9.2 out of 10, Wonderful, (56 reviews)
"Great condo, plenty of room for 3 of us, very quiet and peaceful, love the ice cream shop right next door, would definitely stay here again!"
United States
Jenny R.
The price is NZ$578
includes taxes & fees
14 Aug - 15 Aug
The Lovebird-sleeps 3! Great value on Sanibel-walk to dining, shops and Historic East End Lighthouse

20. Captiva Villa 3221 | Coastal Residence | Great Amenities | Walk to the Beach

Captiva Villa 3221 | Coastal Residence | Great Amenities | Walk to the Beach
Captiva
7.8 out of 10, Good, (10 reviews)
"Property was perfect for an extended weekend getaway. Great location near a beautiful beach."
United States
Janice S.
The price is NZ$839
includes taxes & fees
14 Aug - 15 Aug
Captiva Villa 3221 | Coastal Residence | Great Amenities | Walk to the Beach
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 Flamingo Bay Hotel Reviews

Find out more about Flamingo Bay

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Flamingo Bay holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Flamingo Bay. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Flamingo Bay. Seeing all the best attractions is bound to make you fall in love with Flamingo Bay. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Flamingo Bay short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there holiday rentals in Flamingo Bay?

Yes, there are holiday rentals close to the most popular sights in Flamingo Bay, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Flamingo Bay has to offer?

North Captiva Point House - Boat/Water Taxi Only **NEWLY RENOVATED **: This holiday home rental outside of Flamingo Bay is located on the beach, and has a balcony, a BBQ and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave.

How many holiday rentals will I find in Flamingo Bay?

Choose from 6 Expedia holiday rentals in Flamingo Bay for a memorable holiday.

What can I see and do in Flamingo Bay?

While exploring the area, visit family-friendly sights like Sun Splash Water Park, or get outside and enjoy nature at North Captiva Island Beach. In the wider area, you’ll find Key West Express and Tarpon Point.

What are holiday rentals like in Flamingo Bay?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Flamingo Bay. Holiday rentals offer extras like WiFi and washers and dryers so you'll feel right at home. If you're concerned about a sanitised environment, holiday rentals can provide a sense of security away from shared hotel lifts and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental an attractive choice for a family trip or a small group gathering.