Surfside Vacation Rental - Vacation Rentals in Flamingo

Dolphin Retreat From US $162
         

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8.0 (1 Review)
House
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  • Pet Friendly
Premium Floating Bungalow by Stay Ombi From US $1,417
         

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10.0 (1 Review)
Boat Rental
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  • View
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ From US $530
         

10.0 (162 Reviews)
Condo
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  • TV

Luxury Places to Stay in Flamingo

Over 6724+ Luxury Places to Stay in or Near Flamingo
Little Bay Compound From US $16,123
         

New
House
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Top-Rated Vacation Rentals with a Pool in Flamingo

Over 4737+ Top-Rated Vacation Rentals with a Pool in or Near Flamingo

Pet-Friendly Vacation Rentals in Flamingo

Over 1804+ Pet-Friendly Vacation Rentals in or Near Flamingo
Marathon Vacation Home with Pool, Hot Tub & Movie Theater From US $421
         

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10.0 (3 Reviews)
House
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Yacht Haven Marina From US $376
         

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9.6 (288 Reviews)
Boat Rental
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  • Pet Friendly
Grouper House: 4 Masters/6 BA, Pool/Dock, BoatRamp From US $1,049
         

10.0 (81 Reviews)
House
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  • Pet Friendly
Fla Keys Luxury Houseboat, Prime Location-Steps to Fun, Food & Water Adventures From US $559
         

See More Pet-Friendly Vacation Rentals in Flamingo on PetFriendly.io

Large Vacation Homes & Villas in Flamingo

Over 1312+ Large Vacation Homes & Villas in or Near Flamingo
5 bedroom - Deep Dockage & Heated Pool in Islamorada. From US $1,350
         

Coral Cove From US $319
         

New
House
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The Islands of Islamorada From US $954
         

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9.8 (72 Reviews)
Villa
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4 Bedrooms,large private pool,Great fishing! From US $690
         

8.8 (64 Reviews)
House
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  • Pet Friendly

Wheelchair Accessible Vacation Homes in Flamingo

Over 1607+ Wheelchair Accessible Vacation Homes in or Near Flamingo
Birds Eye Loft Perched Above the Marina 1BR 1BA 5413 From US $347
         

Flamingo Adventures Lodge From US $280
         

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9.0 (14 Reviews)
Cabin
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Top Floor unit with a ocean view! PRIVATELY OWNED From US $275
         

9.8 (134 Reviews)
Condo
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  • Pool
Ocean Front, Marina, Pool/Hot Tub, Private Beach, Bar/Cafe From US $293
         

This Oceanfront Resort HAS IT ALL! From US $245
         

9.0 (27 Reviews)
Condo
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Seaside Escape with Luxe Interior and Ocean Views From US $360
         

9.6 (59 Reviews)
Condo
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  • Pool

Flamingo Vacation Rentals and Airbnb Places to Stay Under $200

Over 536+ Flamingo Vacation Rentals and Airbnb Places to Stay Under $200
Ocean Isles Seaside Oasis From US $190
         

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10.0 (1 Review)
Apartment
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Luxurious Tropical Retreat with Private Tiki Hut From US $149
         

9.8 (19 Reviews)
House
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Waterside Suites & Marina From US $166
         

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9.0 (1286 Reviews)
Hotel
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Great house at walking distance from the ocean. Key Largo-Tavernier. From US $175
         

OCEANFRONT community, perfect condo, sleeps 4 From US $186
         

10.0 (4 Reviews)
Condo
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  • Pool

Instantly Bookable Vacation Homes in Flamingo

Over 4154+ Instantly Bookable Vacation Homes in or Near Flamingo
Lagoon View Retreat 2 Kings Pickleball Marina From US $499
         

9.8 (155 Reviews)
House
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  • Pool
Beautiful Kawama Townhouse From US $638
         

9.8 (145 Reviews)
House
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  • Pool
Waterfront Condo with Boat Slip & Pool Access From US $523
         

9.6 (129 Reviews)
Condo
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  • Pool
Canal side location with beach & pool club membership! From US $370
         

9.6 (89 Reviews)
Condo
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  • Parking
  • Pet Friendly

About Flamingo Vacation Rentals

With more than 6733 Flamingo vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Surfsidevacationrental and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Flamingo.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Surfsidevacationrental Flamingo, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Flamingo. Places to stay near Flamingo are 857.18 ft² on average, with prices averaging $622 a night.

Surfsidevacationrental makes it easy and safe to find and compare vacation rentals in Flamingo with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Flamingo

Type Count
Vacation Homes 4128
Holiday Apartments 601
Hotels with Suites 423
Villas 287
Resorts 190
Cottages 71
Others 24
Cabin Rentals 12
Hostels 1
Ski Chalet Rentals 1

Use these Quick Filters to Find a Vacation Rental in Flamingo

Pro Tip: Surfsidevacationrental makes it easy to compare the best listings on Surfsidevacationrental homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Surfsidevacationrental homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Flamingo.

Weather in Flamingo

View the weather forecast for Flamingo before booking your Flamingo Vacation Rentals to confirm your best time to go.

December - February
High 81°F       Low 64°F
March - May
High 87°F       Low 66°F
June - August
High 91°F       Low 78°F
September - November
High 90°F       Low 71°F

Flamingo Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Flamingo?
How many vacation rentals are available in Flamingo?

Currently, the total number of properties listed in 2026 is over 6733 in the Flamingo area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Flamingo.