Surfer Hotels - Vacation Rentals in Flamingo

Elegant Home with Beach & Dockage! Spectacular Sunsets! in Key Largo From US $1,248
         

9.4 (64 Reviews)
Hotel
  • Air Conditioner
  • Balcony/Terrace
  • Security/Safety
Island Bay Resort in Key Largo From US $336
         

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9.6 (229 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Designated Smoking Area
The Caribbean Resort in Islamorada From US $639
         

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10.0 (174 Reviews)
Hotel
  • Air Conditioner
  • Pool
  • Designated Smoking Area

Luxury Places to Stay in Flamingo

Over 6801+ Luxury Places to Stay in or Near Flamingo
New
House
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Chateau On The Ocean - The Southernmost Shangrila in Islamorada From US $8,960
         

10.0 (2 Reviews)
House
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  • Pet Friendly
Villa familiar en un paraíso in Islamorada From US $7,866
         

New
Villa
  • Air Conditioner
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  • Designated Smoking Area

Top-Rated Vacation Rentals with a Pool in Flamingo

Over 4880+ Top-Rated Vacation Rentals with a Pool in or Near Flamingo
Key Colony Beach oceanview condo, beach + heated pool in Key Colony Beach From US $266
         

Pet-Friendly Vacation Rentals in Flamingo

Over 1859+ Pet-Friendly Vacation Rentals in or Near Flamingo
Dolphin Retreat in Marathon From US $162
         

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8.0 (1 Review)
House
  • Air Conditioner
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  • Pet Friendly
Yacht Haven Marina in Marathon From US $251
         

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9.8 (353 Reviews)
Boat Rental
  • Air Conditioner
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  • Pet Friendly
Grouper House: 4 Masters/6 BA, Pool/Dock, BoatRamp in Marathon From US $896
         

10.0 (87 Reviews)
House
  • Air Conditioner
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  • Pet Friendly
Fla Keys Luxury Houseboat, Prime Location-Steps to Fun, Food & Water Adventures in Tavernier From US $523
         

Luxury Canal Home | Heated Pool & Ocean Access in Marathon From US $589
         

9.8 (59 Reviews)
House
  • Air Conditioner
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  • Pet Friendly
See More Pet-Friendly Vacation Rentals in Flamingo on PetFriendly.io

Large Vacation Homes & Villas in Flamingo

Over 1303+ Large Vacation Homes & Villas in or Near Flamingo
5 bedroom - Deep Dockage & Heated Pool in Islamorada. in Islamorada From US $1,341
         

Coral Cove in Key Colony Beach From US $319
         

New
House
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  • Child Friendly
4 Bedrooms,large private pool,Great fishing! in Key Colony Beach From US $762
         

8.8 (65 Reviews)
House
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  • Parking
  • Pet Friendly
Manatee Bay in Key Colony Beach From US $1,091
         

9.8 (77 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool

Wheelchair Accessible Vacation Homes in Flamingo

Over 1674+ Wheelchair Accessible Vacation Homes in or Near Flamingo
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ in Tavernier From US $463
         

10.0 (169 Reviews)
Condo
  • Air Conditioner
  • Parking
  • TV
Flamingo Adventures Lodge in Flamingo From US $140
         

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8.4 (34 Reviews)
Cabin
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  • View
Ocean Front, Marina, Pool/Hot Tub, Private Beach, Bar/Cafe in Tavernier From US $197
         

This Oceanfront Resort HAS IT ALL! in Key Colony Beach From US $250
         

9.0 (28 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
Seaside Escape with Luxe Interior and Ocean Views in Tavernier From US $424
         

Flamingo Vacation Rentals and Airbnb Places to Stay Under $200

Over 580+ Flamingo Vacation Rentals and Airbnb Places to Stay Under $200
Carpe' Diem Heart of the Fl. Keys Specials in Marathon From US $189
         

8.8 (157 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly
Ocean Isles Seaside Oasis in Marathon From US $190
         

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10.0 (1 Review)
Apartment
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  • Accessibility
  • Security/Safety
Ragged Edge Resort & Marina in Islamorada From US $166
         

9.6 (262 Reviews)
House
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  • Parking
  • Pool
The Keys to Happiness! in Key Colony Beach From US $199
         

10.0 (47 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Great house at walking distance from the ocean. Key Largo-Tavernier. in Tavernier From US $168
         

Instantly Bookable Vacation Homes in Flamingo

Over 4423+ Instantly Bookable Vacation Homes in or Near Flamingo
Lagoon View Retreat 2 Kings Pickleball Marina in Key Largo From US $424
         

9.8 (157 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool

About Flamingo Vacation Rentals

With more than 527 Flamingo vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Surferhotels 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 Surferhotels 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 67.86 ft² on average, with prices averaging US $671 a night.

Surferhotels 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
Hotels 527

Use these Quick Filters to Find a Vacation Rental in Flamingo

Pro Tip: Surferhotels makes it easy to compare the best listings on Surferhotels homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Surferhotels 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 527 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.