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Flamingo Bay Vacation Rentals

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Our top choices for Flamingo Bay vacation 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 CA $151
CA $501 total
includes taxes & fees
Oct 18 - Oct 19
Manatee Lookout Cottages - Boat to Beach, Dock, Pool, Kayaks, Direct Gulf Access

2. Island Inn

Island Inn
3.5 star property
West End
9.4 out of 10, Exceptional, (1,163 reviews)
"Great location"
United States
Nicole
The price is CA $396
CA $441 total
includes taxes & fees
Oct 30 - Oct 31
Island Inn

3. 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

4. Lazy Cuckoo Inn

Lazy Cuckoo Inn
2.0 star property
Fort Myers Beach
8.8 out of 10, Excellent, (301 reviews)
"Great place!"
United States
Bruce
The price is CA $75
CA $129 total
includes taxes & fees
Oct 20 - Oct 21
Lazy Cuckoo Inn

5. Edison Beach House

Edison Beach House
3.5 star property
Fort Myers Beach
9.4 out of 10, Exceptional, (1,943 reviews)
"Great stay."
United States
Angie
The price is CA $180
CA $255 total
includes taxes & fees
Oct 19 - Oct 20
Edison Beach House

6. Sundial Beach Resort & Spa

Sundial Beach Resort & Spa
5.0 star property
Mid Island
8.6 out of 10, Excellent, (2,716 reviews)
"Love the resort and great access to beach"
United States
Lisa Renee
The price is CA $457
CA $603 total
includes taxes & fees
Oct 23 - Oct 24
Sundial Beach Resort & Spa

7. 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 CA $223
CA $866 total
includes taxes & fees
Oct 18 - Oct 19
Bayside Villa 5110 | Upscale Bayfront Residence | In-unit laundry | Walk to the Beach

8. MALU LANI Inn & Marina

MALU LANI Inn & Marina
3.5 star property
Bokeelia
10.0 out of 10, Exceptional, (6 reviews)
"Overall, very friendly Gave me advice about the area Told me what live bands were playing that night Very fun definitely will be back"
United States
Kyle
The price is CA $246
CA $528 total
includes taxes & fees
Oct 27 - Oct 28
MALU LANI Inn & Marina

9. Stunning Modern beach front unit - completely renovated! Includes golf cart!

Stunning Modern beach front unit - completely renovated! Includes golf cart!
Captiva
9.8 out of 10, Exceptional, (129 reviews)
"View was amazing, watched the sunset from the balcony most evenings. The place was clean, and had beach chairs and shelling tools there to use as well as an umbrella. Very enjoyable and relaxing stay!"
United States
Theodore S. E.
The price is CA $390
CA $749 total
includes taxes & fees
Oct 23 - Oct 24
Stunning Modern beach front unit - completely renovated! Includes golf cart!

10. 2 Queen Bed|Nsmk|Cape Coral FL

2 Queen Bed|Nsmk|Cape Coral FL
Caloosahatchee
10.0 out of 10, Exceptional, (154 reviews)
"Had a lovely time here!"
United States
Anonymous traveller
The price is CA $88
CA $98 total
includes taxes & fees
Oct 18 - Oct 19
2 Queen Bed|Nsmk|Cape Coral FL

11. 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 CA $167
CA $295 total
includes taxes & fees
Oct 18 - Oct 19
Southernmost Inn King Suite on Canal

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

Bayside Villa 4224: Bright Corner Unit with Stunning Bay Views
Captiva
9.0 out of 10, Wonderful, (16 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 CA $147
CA $658 total
includes taxes & fees
Oct 18 - Oct 19
Bayside Villa 4224: Bright Corner Unit with Stunning Bay Views

13. 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)
"Great stay here! Clean and spacious. Loved the amenities and the location ease of access."
United States
Brianna L.
The price is CA $115
CA $411 total
includes taxes & fees
Oct 23 - Oct 24
Modern Luxurious Condo, King Bed Suite, Waterfront + Pool, Near Downtown

14. Bayside Villa 4116 | Newly Renovated Marina View Residence | Walk to the Beach

Bayside Villa 4116 | Newly Renovated Marina View Residence | Walk to the Beach
Captiva
8.6 out of 10, Excellent, (9 reviews)
"My husband and I enjoyed our stay here. The location was perfect, with restaurants and shops being within easy walking distance. The pool was beautiful and never crowded. "
United States
Maureen J.
The price is CA $223
CA $738 total
includes taxes & fees
Oct 18 - Oct 19
Bayside Villa 4116 | Newly Renovated Marina View Residence | Walk to the Beach

15. 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)
"Great location to the beach"
United States
Robin H.
The price is CA $240
CA $618 total
includes taxes & fees
Oct 18 - Oct 19
Gorgeous Coastal Cottage "Ibis" Minutes to the beach and free bikes! JULY SAVINGS

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 CA $212
CA $352 total
includes taxes & fees
Oct 18 - Oct 19
Charming 1-bedroom apartment in Bokeelia with WiFi, AC, pool & heated spa

17. 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, (96 reviews)
"This is a beautiful home, nicely decorated and well maintained, on a canal on Pine Island. The canal provided easy access to waterways making Sanibel and Captiva Islands a short trip away. There was plenty of room to park our boat trailer during our stay. Check-in was easy and the host was quick to respond to a couple of questions we had upon arrival. We enjoyed our stay and look forward to returning."
United States
Becky W.
The price is CA $225
CA $630 total
includes taxes & fees
Nov 7 - Nov 8
Fisherman's Delight With Heated Salt Swimming Pool and a new Boat Lift

18. 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 CA $236
CA $833 total
includes taxes & fees
Oct 18 - Oct 19
Captiva Villa 3213 | Chic Residence | Great Amenities | Walk to the Beach

19. Marina Villa 603 | Spacious Coastal Residence | Great Amenities | Walk to the Beach

Marina Villa 603 | Spacious Coastal Residence | Great Amenities | Walk to the Beach
Captiva
8.6 out of 10, Excellent, (13 reviews)
"We stayed with our 2 grandchildren and loved the location and the full kitchen. "
United States
Cheryl G.
The price is CA $560
CA $1,287 total
includes taxes & fees
Oct 18 - Oct 19
Marina Villa 603 | Spacious Coastal Residence | Great Amenities | Walk to the Beach

20. coastal chic cottage "Heron" minutes to the beach! JULY SAVINGS!

coastal chic cottage "Heron" minutes to the beach! JULY SAVINGS!
West End
9.2 out of 10, Wonderful, (44 reviews)
"This was my second stay . It’s so amazing and the location is perfect !!!! We will be back !"
United States
EMILY B.
The price is CA $240
CA $656 total
includes taxes & fees
Oct 21 - Oct 22
coastal chic cottage "Heron" minutes to the beach! JULY SAVINGS!
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

Everything you need to know about Flamingo Bay vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Flamingo Bay vacation rental for you. At Expedia, you can take your pick from private vacation 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Flamingo Bay vacation 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Flamingo Bay vacation rentals we have selected for you start as low as CA $129 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 vacation 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 vacation.

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 vacation rentals in Flamingo Bay?

Yes, we offer vacation rentals near top local attractions in Flamingo Bay, or you can select a more secluded option if you're looking for relaxation.

What are some of the best vacation home rentals in Flamingo Bay?

OCT 17-24, NOV 7-14 and DEC 5-12 available Discounted Rates!! Beach 🏖️ 2min walk🩴: Visitors like this Flamingo Bay vacation home rental. It is located near the beach and has an outdoor pool, a balcony, and a barbecue grill 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 you can cook with friends or family. You can relax into your vacation with a selection of games and a hot tub.

How many vacation rentals will I find in Flamingo Bay?

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

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 larger area, you’ll find Key West Express and Jensen’s Marina.

What are vacation rentals like in Flamingo Bay?

Vacation rentals are private accommodations you can reserve for a couple days or more in Flamingo Bay. Vacation rentals offer extras like kitchens and laundry facilities so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, vacation rentals can offer a sense of safety away from public hotel elevators and lobbies bustling with people while still allowing you to travel. You'll also have more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a popular option for a small group gathering.