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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$622
includes taxes & fees
1 Oct - 2 Oct
Manatee Lookout Cottages - Boat to Beach, Dock, Pool, Kayaks, Direct Gulf Access

2. Matlacha Tiny Village

Matlacha Tiny Village
3.0 star property
Matlacha
9.0 out of 10, Wonderful, (297 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 NZ$393
includes taxes & fees
30 Sept - 1 Oct
Matlacha Tiny Village

3. Studio with Patio - Turtle Cove - Welcome to our stunning, newly renovated studio condo!

Studio with Patio - Turtle Cove - Welcome to our stunning, newly renovated studio condo!
Matlacha
9.8 out of 10, Exceptional, (9 reviews)
"This is a wonderful property with a fantastic manager -Stacey. It is beautiful with great amenities and a great location."
United States
David H.
The price is NZ$281
includes taxes & fees
11 Oct - 12 Oct
Studio with Patio - Turtle Cove - Welcome to our stunning, newly renovated studio condo!

4. 2 Queen Bed|Nsmk|Cape Coral FL

2 Queen Bed|Nsmk|Cape Coral FL
Caloosahatchee
10.0 out of 10, Exceptional, (151 reviews)
"Had a lovely time here!"
United States
Anonymous traveller
The price is NZ$120
includes taxes & fees
28 Sept - 29 Sept
2 Queen Bed|Nsmk|Cape Coral FL

5. Lazy Cuckoo Inn

Lazy Cuckoo Inn
2.0 star property
Fort Myers Beach
8.8 out of 10, Excellent, (299 reviews)
"Great place!"
United States
Bruce
The price is NZ$147
includes taxes & fees
1 Oct - 2 Oct
Lazy Cuckoo Inn

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$1,045
includes taxes & fees
28 Sept - 29 Sept
Bayside Villa 5110 | Upscale Bayfront Residence | In-unit laundry | Walk to the Beach

7. Cape Coral FL | King bed

Cape Coral FL | King bed
Caloosahatchee
10.0 out of 10, Exceptional, (196 reviews)
"Views of the lake from this hotel are wonderful. The pool was enjoyable as well."
United States
Anonymous traveller
The price is NZ$126
includes taxes & fees
28 Sept - 29 Sept
Cape Coral FL | King bed

8. 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, (15 reviews)
"Clean property, easy access. Good kitchen supplies. It was nice to be staying on the island and close to the beach."
United States
Louis
The price is NZ$813
includes taxes & fees
28 Sept - 29 Sept
Bayside Villa 4224: Bright Corner Unit with Stunning Bay Views

9. Southernmost Inn King Suite on Canal

Southernmost Inn King Suite on Canal
Saint James City
10.0 out of 10, Exceptional, (19 reviews)
"Great spot. We have stayed multiple times, love the location. Everything has been great and look forward to going back! "
United States
Tracy L.
The price is NZ$366
includes taxes & fees
1 Oct - 2 Oct
Southernmost Inn King Suite on Canal

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

11. Island Inn

Island Inn
3.5 star property
West End
9.4 out of 10, Exceptional, (1,156 reviews)
"Great location"
United States
Nicole
The price is NZ$402
includes taxes & fees
28 Sept - 29 Sept
Island Inn

12. 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$443
includes taxes & fees
4 Oct - 5 Oct
Charming 1-bedroom apartment in Bokeelia with WiFi, AC, pool & heated spa

13. 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)
"Great villa for 2 people. The place was clean, well stocked and comfortable. The pool was lovely. Check in / check out was seamless. Would definitely book again."
United States
Connie A.
The price is NZ$1,012
includes taxes & fees
28 Sept - 29 Sept
Captiva Villa 3213 | Chic Residence | Great Amenities | Walk to the Beach

14. 1BR condo - Steps to the Gulf - Colony Inn 55

1BR condo - Steps to the Gulf - Colony Inn 55
East End
10.0 out of 10, Exceptional, (10 reviews)
"Spent 5 wonderful days at Colony Inn."
United States
Norman G.
1BR condo - Steps to the Gulf - Colony Inn 55

15. 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$703
includes taxes & fees
1 Oct - 2 Oct
Coastal Chic Cottage "Sandpiper" minutes to the beach! Free bikes

16. 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$506
includes taxes & fees
7 Oct - 8 Oct
Modern Luxurious Condo, King Bed Suite, Waterfront + Pool, Near Downtown

17. The Chic Shack: Elevated Beachfront Luxury & Designer Views at Beach Villa 2414

The Chic Shack: Elevated Beachfront Luxury & Designer Views at Beach Villa 2414
Captiva
9.4 out of 10, Exceptional, (34 reviews)
"The place was very nice ."
United States
Cathy S.
The price is NZ$1,055
includes taxes & fees
28 Sept - 29 Sept
The Chic Shack: Elevated Beachfront Luxury & Designer Views at Beach Villa 2414

18. Edison Beach House

Edison Beach House
3.5 star property
Fort Myers Beach
9.4 out of 10, Exceptional, (1,921 reviews)
"Great stay."
United States
Angie
The price is NZ$321
includes taxes & fees
28 Sept - 29 Sept
Edison Beach House

19. Waterfront Condo with Pool & Boat Slip

Waterfront Condo with Pool & Boat Slip
Caloosahatchee
10.0 out of 10, Exceptional, (26 reviews)
"Great location! Great kitchen! Very comfortable beds. Pool area and pool were the best. Great dock. We had the best stay at Seatuit."
United States
Mark L.
The price is NZ$586
includes taxes & fees
1 Oct - 2 Oct
Waterfront Condo with Pool & Boat Slip

20. 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, (55 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$531
includes taxes & fees
28 Sept - 29 Sept
Newly remodeled Parrot Nest Toucan Cottage! Walk to beach, shops, restaurants!
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.