Search Holiday Rentals in Flamingo

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Top Holiday Rentals in Flamingo

Breezy Palms Resort

2.5 star property
8.8 out of 10, Excellent, (488)
"Laid back atmosphere with renovated rooms."
The price is 1 523 kr
includes taxes & fees
16 Jul - 17 Jul
Breezy Palms Resort

Treasure Harbor

3.0 star property
9.0 out of 10, Wonderful, (82)
"Very clean and great atmosphere "
The price is 2 774 kr
includes taxes & fees
6 Jul - 7 Jul
Treasure Harbor

The Islands of Islamorada

4.0 star property
9.8 out of 10, Exceptional, (61)
"Absolutely outstanding resort. Legitimate 5 star property. "
The price is 6 414 kr
includes taxes & fees
8 Jul - 9 Jul
The Islands of Islamorada

Island Bay Resort

2.5 star property
10.0 out of 10, Exceptional, (121)
"Amazing property and wonderful owners. Super nice people and definitely will be returning."
Island Bay Resort

Key Largo Cottages

2.5 star property
9.4 out of 10, Exceptional, (20)
"The stay was great and the property manager Jenn was amazing. Would stay again"
Key Largo Cottages

Two Panoramic Ocean Views from the Living room and Master Bedroom in this Condo

9.8 out of 10, Exceptional, (217)
"We enjoyed our short stay but looking forward to going back."
Two Panoramic Ocean Views from the Living room and Master Bedroom in this Condo

Next availability from May 18th, 2024 - The Last Resort, Islamorada - MM76.7

10.0 out of 10, Exceptional, (82)
"Everything just great except need better vaccum"
Next availability from May 18th, 2024 - The Last Resort, Islamorada - MM76.7

Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool

9.8 out of 10, Exceptional, (61)
"Enjoyed our stay. Lots to do if you’re wanting a relaxing day or a day of swimming, tennis, walking or cycling. "
Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool

Summer Deals! OCEANFRONT Lux 1300sf with Stunning Views & All Amenities of home!

9.6 out of 10, Exceptional, (286)
"We enjoyed the amenities at the Yacht Club very much. It was never too busy. Very quiet at night. Close to other entertainment and good restaurants. "
Summer Deals! OCEANFRONT Lux 1300sf with Stunning Views & All Amenities of home!

Condo in the Keys

5.0 star property
9.0 out of 10, Wonderful, (7)
"Thoroughly enjoyed our stay! The pool, beach area and pickleball courts were fantastic! Also enjoyed the premium cable. "
Condo in the Keys

Waterfront Tiny House w Pool, Beach, and Boat Dock

9.6 out of 10, Exceptional, (55)
"We stayed here in April 2025 - perfect location with a great patio overlooking the waterfront harbor, perfect for us. Everything you need is a short drive - grocery Publix is close enough to walk to. The tiny house is adorable and clean, well stocked kitchen - We found great place to hike /Hamock State Park and Rowell’s was a great place to swim "
The price is 4 445 kr
includes taxes & fees
22 Jul - 23 Jul
Waterfront Tiny House w Pool, Beach, and Boat Dock

OCEANFRONT ANGLERS REEF in ISLAMORADA -Pool, Dock, Beach, Kayaks, Paddle Boards

10.0 out of 10, Exceptional, (182)
"Rodger and Linda is home and Islamorada is wonderful. They are unbelievably accommodating property owners and made the trip extra special. I look forward to returning and staying there again."
OCEANFRONT ANGLERS REEF in ISLAMORADA -Pool, Dock, Beach, Kayaks, Paddle Boards

Ocean Front Private Beach, Pool/Hot Tub, Pool Bar, Marina with Cafe

9.8 out of 10, Exceptional, (181)
"Nice place, lots to do, great location, great views"
Ocean Front Private Beach, Pool/Hot Tub, Pool Bar, Marina with Cafe

Kawama Yacht Club - 2 Bedrooms with a Private Ocean Front Beach

9.8 out of 10, Exceptional, (129)
"Jorge was the consummate host! We had requested additional items to enhance our stay, and he was agreeable without hesitation. The condo was in a great location and suited all our needs. We had a lovely stay!! "
Kawama Yacht Club - 2 Bedrooms with a Private Ocean Front Beach

Anchorage Resort & Yacht Club

3.0 star property
8.6 out of 10, Excellent, (287)
"It’s a good place to stay with family"
The price is 2 623 kr
includes taxes & fees
6 Jul - 7 Jul
Anchorage Resort & Yacht Club

Lady Blue Yacht in FL KEYS

7.0 out of 10, Good, (7)
"We enjoyed our stay from beginning to end. The checking and check out was very smooth. Thank you so much!"
The price is 3 831 kr
includes taxes & fees
6 Jul - 7 Jul
Lady Blue Yacht in FL KEYS

New Tiny Home- Paddle Boards, Kayaks, Pool, Marina

9.4 out of 10, Exceptional, (68)
"Great tiny house, enjoyed our stay"
The price is 4 132 kr
includes taxes & fees
22 Jul - 23 Jul
New Tiny Home- Paddle Boards, Kayaks, Pool, Marina

Cozy Waterfront Retreat w/ Private Boat Dock + Tiki

9.2 out of 10, Wonderful, (14)
"The property was nice and having the dock behind the trailer was very convenient."
Cozy Waterfront Retreat w/ Private Boat Dock + Tiki

Oceanfront Key Largo Paradise with Private Beach~Pool~Tennis~Marina & more....

10.0 out of 10, Exceptional, (261)
"The unit and location was perfect ! Great stay and we will be back next year !"
Oceanfront Key Largo Paradise with Private Beach~Pool~Tennis~Marina & more....

Kings Kamp

2.5 star property
8.6 out of 10, Excellent, (21)
"Kings Kamp was a charming stay. The owners were friendly and made the stay easy"
Kings Kamp
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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