Flamingo Bay Holiday Rentals

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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Flamingo Bay holiday rentals

An infinity pool with chairs and tables, a palm tree, and a sunset view.

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, (4 reviews)
"Great location. Nice property. Clean and comfortable."
United States
Mary Ellen I.
The price is NZ$620
includes taxes & fees
10 Dec - 11 Dec
Manatee Lookout Cottages - Boat to Beach, Dock, Pool, Kayaks, Direct Gulf Access
A beachside area with colorful beach houses, a dock, and a sandy beach.

2. Matlacha Tiny Village

Matlacha Tiny Village
3.0 star property
Matlacha
9.0 out of 10, Wonderful, (299 reviews)
"Such a cute place that we have never heard of! Walked to cute tiny shops, got awesome bbq……… very quaint and quiet. Had a great time."
United States
Shannon
The price is NZ$397
includes taxes & fees
15 Nov - 16 Nov
Matlacha Tiny Village
A pool area with lounge chairs and umbrellas, a beach with umbrellas and lounge chairs, and palm trees.

3. Sundial Beach Resort & Spa

Sundial Beach Resort & Spa
5.0 star property
Mid Island
8.6 out of 10, Excellent, (2,720 reviews)
"Great trip, beautiful island and great location!"
United States
Jeremy
The price is NZ$600
includes taxes & fees
10 Dec - 11 Dec
Sundial Beach Resort & Spa
A beach with a view of the ocean and a sunset.

4. Island Inn

Island Inn
3.5 star property
West End
9.4 out of 10, Exceptional, (1,169 reviews)
"Upon arrival, the front desk was very helpful explaining everything in detail. The room was very clean & spacious and had everything we needed for our stay. The location on the beach and the view was AMAZING!! We would definitely stay here again…HIGHLY RECOMMEND!!!"
United States
Elizbeth
The price is NZ$435
includes taxes & fees
12 Nov - 13 Nov
Island Inn
A balcony with a TV, a chair, and a view of a beach with a pier.

5. Edison Beach House

Edison Beach House
3.5 star property
Fort Myers Beach
9.4 out of 10, Exceptional, (1,966 reviews)
"Best place ever"
United States
Joshua
The price is NZ$375
includes taxes & fees
17 Nov - 18 Nov
Edison Beach House
A modern living room with a flat-screen TV, a floor lamp, a dining table, and a sofa.

6. Lazy Cuckoo Inn

Lazy Cuckoo Inn
2.0 star property
Fort Myers Beach
8.8 out of 10, Excellent, (311 reviews)
"Great location. Great night sleep"
United States
Stephanie
The price is NZ$174
includes taxes & fees
12 Dec - 13 Dec
Lazy Cuckoo Inn
A beach with a prominent dead tree trunk, sandy shore, and calm sea.

7. MALU LANI Inn & Marina

MALU LANI Inn & Marina
3.5 star property
Bokeelia
10.0 out of 10, Exceptional, (6 reviews)
"Beautiful property, peaceful, clean rental. Super responsive owner and all the things you need. Perfect location for boaters. Loved this stay and would definitely rent again! "
United States
April
The price is NZ$697
includes taxes & fees
12 Nov - 13 Nov
MALU LANI Inn & Marina
A modern kitchen with a central island, stainless steel appliances, and a decorative backsplash.

8. 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, (41 reviews)
"We absolutely loved the location and the property. Already looking forward to coming back next year. Condo was clean, lots of space and enjoyed the screened in porch. Host is very attentive and alway quick to reply. Thanks for such a special vacation!"
United States
Buffey H.
The price is NZ$484
includes taxes & fees
19 Nov - 20 Nov
Modern Luxurious Condo, King Bed Suite, Waterfront + Pool, Near Downtown
A spacious living room with a grey sofa, striped armchair, and a woven coffee table. Large windows offer a view of a tropical garden.

9. Driftwood Inn

Driftwood Inn
4.0 star property
Mid Island
10.0 out of 10, Exceptional, (11 reviews)
"Great place to stay on sanibel"
United States
Terri
The price is NZ$816
includes taxes & fees
15 Nov - 16 Nov
Driftwood Inn
An aerial view of a beach with rows of blue umbrellas and beach chairs, a sandy shoreline, and a path leading through the beach area.

10. 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$991
includes taxes & fees
12 Nov - 13 Nov
Bayside Villa 5110 | Upscale Bayfront Residence | In-unit laundry | Walk to the Beach
A beach with a clear sky, palm trees, and a sunlit ocean.

11. GullWing Beach Resort

GullWing Beach Resort
3.5 star property
South Island
9.6 out of 10, Exceptional, (987 reviews)
"Gullwing is an excellent beach front condo property. Very well maintained, friendly staff and close to amenities."
United States
Jennifer
The price is NZ$996
includes taxes & fees
12 Dec - 13 Dec
GullWing Beach Resort
A wooden deck with a table and chairs overlooking a body of water, palm trees, and a house in the background.

12. 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$370
includes taxes & fees
15 Nov - 16 Nov
Southernmost Inn King Suite on Canal
An aerial view of a beach with rows of blue umbrellas and beach chairs, a sandy shoreline, and a path leading through the beach area.

13. 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$853
includes taxes & fees
12 Nov - 13 Nov
Bayside Villa 4208 | Stunning Harbourview Residence| Walk to the Beach
A hotel room with a bed, a nightstand, a lamp, a framed picture on the wall, and a door leading to a bathroom.

14. Lovers Key Resort

Lovers Key Resort
3.0 star property
Fort Myers Beach
8.8 out of 10, Excellent, (1,097 reviews)
"Room location had a amazing view"
United States
Joanne
The price is NZ$529
includes taxes & fees
12 Nov - 13 Nov
Lovers Key Resort
An aerial view of a beach with rows of blue umbrellas and beach chairs, a sandy shoreline, and a path leading through the beach area.

15. Beach Villa 2011-Stunning Beachfront Residence

Beach Villa 2011-Stunning Beachfront Residence
Captiva
9.6 out of 10, Exceptional, (7 reviews)
"We enjoyed our stay. The villa met our expectations. We liked the beach access and the pool. "
United States
Deb E.
The price is NZ$1,007
includes taxes & fees
12 Nov - 13 Nov
Beach Villa 2011-Stunning Beachfront Residence
A pool with a metal railing, surrounded by lush greenery and a covered area with a metal frame.

16. 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$425
includes taxes & fees
12 Nov - 13 Nov
Charming 1-bedroom apartment in Bokeelia with WiFi, AC, pool & heated spa
A beach with a single seashell in the foreground and two people in the background.

17. Gorgeous Coastal Cottage "Ibis" Minutes to the beach and free bikes! JULY SAVINGS

Gorgeous Coastal Cottage "Ibis" Minutes to the beach and free bikes! JULY SAVINGS
West End
9.4 out of 10, Exceptional, (47 reviews)
"Loved the cottage! We had a wonderful and pleasant stay. Everything was comfortable and enjoyable, and we would definitely stay here again. We look forward to coming back!"
United States
Erica C.
The price is NZ$815
includes taxes & fees
17 Nov - 18 Nov
Gorgeous Coastal Cottage "Ibis" Minutes to the beach and free bikes! JULY SAVINGS
A spacious patio with a dining table and chairs, a sofa, and a ceiling fan.

18. 3BR Coastal retreat in peaceful Bokeelia with pool, bikes, ping pong and fishing

3BR Coastal retreat in peaceful Bokeelia with pool, bikes, ping pong and fishing
Bokeelia
10.0 out of 10, Exceptional, (11 reviews)
"Great property, very clean and host was extremely helpful. Great quiet neighborhood with friendly neighbors."
United States
Neal G.
The price is NZ$716
includes taxes & fees
12 Nov - 13 Nov
3BR Coastal retreat in peaceful Bokeelia with pool, bikes, ping pong and fishing
A covered swimming pool with a clear view of the surrounding area, including a body of water and greenery.

19. Fisherman's Delight With Heated Salt Swimming Pool and a new Boat Lift

Fisherman's Delight With Heated Salt Swimming Pool and a new Boat Lift
St James City
9.6 out of 10, Exceptional, (97 reviews)
"We really enjoyed our stay. The pool and location was amazing. Would definitely rent again."
United States
Lindsay F.
The price is NZ$938
includes taxes & fees
1 Dec - 2 Dec
Fisherman's Delight With Heated Salt Swimming Pool and a new Boat Lift
An aerial view of a beach with rows of blue umbrellas and beach chairs, a sandy shoreline, and a path leading through the beach area.

20. Beach Villa 2426 | Stunning Beachfront Residence on Captiva Island

Beach Villa 2426 | Stunning Beachfront Residence on Captiva Island
Captiva
9.6 out of 10, Exceptional, (26 reviews)
"There were a few minor issues, but for the most part, our stay was enjoyable. "
United States
Ronald
The price is NZ$1,267
includes taxes & fees
12 Nov - 13 Nov
Beach Villa 2426 | Stunning Beachfront Residence on Captiva Island
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

A hotel room with two beds, a wooden headboard, a nightstand with a lamp, and a window with curtains.
Holiday Inn Express Cape Coral-Fort Myers Area by IHG

Holiday Inn Express Cape Coral-Fort Myers Area by IHG

Holiday Inn Express Cape Coral-Fort Myers Area by IHG
Caloosahatchee

10/10 Excellent

We were a bit worried when we saw how close to the mai. Road it is but a room at the top facing the car park was excellent. Even had a useable balcony with distant water views. 2 bar/restaurants just out the back were great with good discounts for staying here. Pool was great. All round, recommended.
Australia
John
Reviewed February 28, 2025
Holiday Inn Express Cape Coral-Fort Myers Area by IHG

Find out more about Flamingo Bay

Everything you need to know about Flamingo Bay holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Flamingo Bay holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Flamingo Bay holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Flamingo Bay holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Flamingo Bay. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Flamingo Bay holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Flamingo Bay holiday rentals we have selected for you start as low as NZ$174 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Flamingo Bay rentals

At Expedia, we put the best Flamingo Bay holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Flamingo Bay rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Flamingo Bay holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Flamingo Bay. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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?

OCT 17-24, NOV 7-14 and DEC 5-12 available Discounted Rates!! Beach 🏖️ 2min walk🩴: This holiday home rental outside of Flamingo Bay is located near the beach, and has an outdoor pool, a balcony and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a selection of games and 1 hot tub.

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 Jensen’s Marina.

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.