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Flamingo Bay Vacation Rentals

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Our top choices for Flamingo Bay vacation rentals

1. Matlacha Tiny Village

Matlacha Tiny Village
3.0 star property
Matlacha
8.8 out of 10, Excellent, (296 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 $183
CA $308 total
includes taxes & fees
Sep 7 - Sep 8
Matlacha Tiny Village

2. Matlacha/Cape Coral - Kokopelli House - a three-story Key West style residence

Matlacha/Cape Coral - Kokopelli House - a three-story Key West style residence
Matlacha
9.8 out of 10, Exceptional, (64 reviews)
"Great stay, would definitely go back! "
United States
Chad N.
The price is CA $644
CA $1,509 total
includes taxes & fees
Sep 9 - Sep 10
Matlacha/Cape Coral - Kokopelli House - a three-story Key West style residence

3. 50’ of Dock for your boats. Hot tub, Boatlift, walk 2 restaurants Xtra parking.

50’ of Dock for your boats. Hot tub, Boatlift, walk 2 restaurants Xtra parking.
Matlacha
10.0 out of 10, Exceptional, (42 reviews)
"Excellent!"
United States
Tim A.
The price is CA $309
CA $717 total
includes taxes & fees
Sep 14 - Sep 15
50’ of Dock for your boats. Hot tub, Boatlift, walk 2 restaurants Xtra parking.

4. Perfect Getaway, Anytime of Year, Sunny, Clean, Spacious & Ideally Located!

Perfect Getaway, Anytime of Year, Sunny, Clean, Spacious & Ideally Located!
Pelican
10.0 out of 10, Exceptional, (36 reviews)
"Yes Great location . Close to stores and restaurants . Pool could have been better if Had a cover temp went down over nite."
United States
Rickie D.
The price is CA $189
CA $582 total
includes taxes & fees
Sep 8 - Sep 9
Perfect Getaway, Anytime of Year, Sunny, Clean, Spacious & Ideally Located!

5. 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 CA $90
CA $221 total
includes taxes & fees
Sep 9 - Sep 10
Studio with Patio - Turtle Cove - Welcome to our stunning, newly renovated studio condo!

6. Boat Dock & Patio: Canal-Front St James City Home!

Boat Dock & Patio: Canal-Front St James City Home!
St. James City
10.0 out of 10, Exceptional, (18 reviews)
"It’s was so great! My family and I enjoyed it. Family-Friendly and had everything we needed felt right at home."
United States
Casey W.
The price is CA $122
CA $485 total
includes taxes & fees
Sep 7 - Sep 8
Boat Dock & Patio: Canal-Front St James City Home!

7. 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, (95 reviews)
"Beautiful home and warm pool conviently right on the canal with a boat lift! The host was very helpful!! We definitely will be back!! "
United States
Jennifer C.
The price is CA $276
CA $683 total
includes taxes & fees
Oct 1 - Oct 2
Fisherman's Delight With Heated Salt Swimming Pool and a new Boat Lift

8. 3-bedroom house in charming Saint James City with Canal Views!

3-bedroom house in charming Saint James City with Canal Views!
Saint James City
10.0 out of 10, Exceptional, (11 reviews)
"Nice place with good fishing in the canal. "
United States
Joshua A.
The price is CA $329
CA $783 total
includes taxes & fees
Sep 22 - Sep 23
3-bedroom house in charming Saint James City with Canal Views!

9. King Suite on Canal

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 $325
CA $497 total
includes taxes & fees
Sep 10 - Sep 11
King Suite on Canal

10. 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, (14 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 CA $145
CA $642 total
includes taxes & fees
Sep 12 - Sep 13
Bayside Villa 4224: Bright Corner Unit with Stunning Bay Views

11. Villa Sol: Premium 2BR Beachfront Corner Unit at Beach Villa 2001

Villa Sol: Premium 2BR Beachfront Corner Unit at Beach Villa 2001
Captiva
9.8 out of 10, Exceptional, (25 reviews)
"Very clean and in a great location"
United States
Brian C.
The price is CA $245
CA $889 total
includes taxes & fees
Sep 7 - Sep 8
Villa Sol: Premium 2BR Beachfront Corner Unit at Beach Villa 2001

12. 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, (32 reviews)
"Such cute condo in a great location with amazing sunsets."
United States
Doug H.
The price is CA $206
CA $833 total
includes taxes & fees
Sep 7 - Sep 8
The Chic Shack: Elevated Beachfront Luxury & Designer Views at Beach Villa 2414

13. Spacious 5-Bedroom Captiva Home with Private Pool & Spa

Spacious 5-Bedroom Captiva Home with Private Pool & Spa
Captiva
9.8 out of 10, Exceptional, (52 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: Great location, the layout of the rooms was perfect for a large family and the management group was extremely responsive whenever we had a concern."
United States
bob v.
The price is CA $1,499
CA $3,503 total
includes taxes & fees
Oct 3 - Oct 4
Spacious 5-Bedroom Captiva Home with Private Pool & Spa

14. 3BR Cottage with Private Pool & Spa, Steps to the Beach

3BR Cottage with Private Pool & Spa, Steps to the Beach
Captiva
9.6 out of 10, Exceptional, (23 reviews)
"Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: We stay on Captiva once a year, and had skipped the last 2 due to the Pandemic. It is our favorite place and the Village makes it work it. Captiva Cutie is a great house. A little small for 6 adults, but it worked really well. The only hiccup was...
United States
susan t.
The price is CA $485
CA $1,531 total
includes taxes & fees
Sep 26 - Sep 27
3BR Cottage with Private Pool & Spa, Steps to the Beach

15. 4BR Captiva Home with Private Pool & Steps to the Beach

4BR Captiva Home with Private Pool & Steps to the Beach
Captiva
9.8 out of 10, Exceptional, (49 reviews)
"Great stay, close to beach, good beach amenities, comfortable home."
United States
Dana P.
The price is CA $588
CA $1,749 total
includes taxes & fees
Sep 7 - Sep 8
4BR Captiva Home with Private Pool & Steps to the Beach

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 $208
CA $429 total
includes taxes & fees
Sep 5 - Sep 6
Charming 1-bedroom apartment in Bokeelia with WiFi, AC, pool & heated spa

17. 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, (10 reviews)
"Property and house were beautiful, clean, quiet. Everything was top notch. Would definitely book again."
United States
Erik B.
The price is CA $177
CA $541 total
includes taxes & fees
Sep 9 - Sep 10
3BR Coastal retreat in peaceful Bokeelia with pool, bikes, ping pong and fishing

18. Waterfront Home: Private Pool & Stunning Sea Views

Waterfront Home: Private Pool & Stunning Sea Views
Pelican
10.0 out of 10, Exceptional, (8 reviews)
"Home was spotless. Loved the layout and view "
United States
Jo-Ann
The price is CA $165
CA $658 total
includes taxes & fees
Sep 17 - Sep 18
Waterfront Home: Private Pool & Stunning Sea Views

19. Fabulous 5 BR Waterfront Villa for Your Perfect Dream Vacation!

Fabulous 5 BR Waterfront Villa for Your Perfect Dream Vacation!
Pelican
9.8 out of 10, Exceptional, (50 reviews)
"Wonderful pool, lanai, view. Great family fun vacation. "
United States
Mary Kay S.
The price is CA $323
CA $1,657 total
includes taxes & fees
Sep 6 - Sep 7
Fabulous 5 BR Waterfront Villa for Your Perfect Dream Vacation!

20. 3BR Beachfront Captiva Home with Private Pool & 120’ Gulf Frontage

3BR Beachfront Captiva Home with Private Pool & 120’ Gulf Frontage
Captiva
9.0 out of 10, Wonderful, (34 reviews)
"Everything was great."
United States
Marvin G.
The price is CA $1,108
CA $2,661 total
includes taxes & fees
Sep 7 - Sep 8
3BR Beachfront Captiva Home with Private Pool & 120’ Gulf Frontage
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 vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation 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 or room. 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 vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . 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 . 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 vacation rental 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 vacation 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 short-term rentals, that won’t be hard to do.

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?

Labor Day, XMas🎄Available- Beach 🏖️ 2min walk🩴: You might want to consider this vacation home rental near Flamingo Bay, which 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 Tarpon Point.

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.