
Flamingo Holiday Rentals
- Change your mindBook hotels with free cancellation
- Be pickySearch almost a million properties worldwide
Check prices for these dates
Our top choices for Flamingo holiday rentals

1. Breezy Palms Resort
Breezy Palms Resort
2. Treasure Harbor
Treasure Harbor
3. Anchorage Resort & Yacht Club
Anchorage Resort & Yacht Club
4. Florida Keys Getaway - Slps 4 - Ocean View
Florida Keys Getaway - Slps 4 - Ocean View
5. Cozy bedroom near Florida Keys
Cozy bedroom near Florida Keys
6. Dazzling Ocean View Suite w/heated pool, beach, marina, tennis/pickleball
Dazzling Ocean View Suite w/heated pool, beach, marina, tennis/pickleball
7. Paradise Palms | 2 Balconies | Ocean Pointe 1206
Paradise Palms | 2 Balconies | Ocean Pointe 1206
8. Coastal Joy | Ocean View 2BR | Ocean Pointe 3412
Coastal Joy | Ocean View 2BR | Ocean Pointe 3412
9. Aqua Vista | Ocean View 2BR | Ocean Pointe 3307
Aqua Vista | Ocean View 2BR | Ocean Pointe 3307
10. Ocean Pointe Ocean View w/heated pool beach marina
Ocean Pointe Ocean View w/heated pool beach marina
11. 2BR Oceanfront Suite w/ Beach & Marina Access
2BR Oceanfront Suite w/ Beach & Marina Access
12. Ocean view condo with balcony/marina view
Ocean view condo with balcony/marina view
13. Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
14. Your Happy Place - gorgeous 2 bed/2 bath oceanfront suite with full kitchen
Your Happy Place - gorgeous 2 bed/2 bath oceanfront suite with full kitchen
15. Starfish Seas | Ocean View | Ocean Pointe 1302
Starfish Seas | Ocean View | Ocean Pointe 1302
16. Serene Oceanfront Keys Condo
Serene Oceanfront Keys Condo
17. Amazing Ocean view condo
Amazing Ocean view condo
18. Cozy 1-bedroom apartment with kitchen in peaceful Tavernier/Key largo
Cozy 1-bedroom apartment with kitchen in peaceful Tavernier/Key largo
19. Sunrise Sanctuary | Top Floor | Ocean Pointe 2415
Sunrise Sanctuary | Top Floor | Ocean Pointe 2415
20. Boho Chic | Steps to Pool | Ocean Pointe 3214
Boho Chic | Steps to Pool | Ocean Pointe 3214Find holiday rentals that suit your style
Top Flamingo Hotel Reviews

Floridian Hotel
Find out more about Flamingo
You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Flamingo holiday 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. 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 holiday just got upgraded.
As much as you love your vacation rental, it’s always good to get out and explore to soak up Flamingo. 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 Flamingo. Seeing all the best attractions is bound to make you fall in love with Flamingo. Who knows, you may even be tempted to extend your 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 holiday 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 Flamingo short-term rentals, that won’t be hard to do.




































































