
Private Pool Homes
Nothing is better than your own private sanctuary to swim in after a long day exploring the Keys or playing on the beach and in the ocean. Come home to your home-away-from-home and lounge near the pool while the kids play and the grill warms for dinner. These awesome Florida Keys rentals with private pools are truly a relaxation haven and are expertly maintained by certified pool technicians throughout the year.
Sort by:
Casa Playa ~ Elite Luxury Pool Home ~ Includes Kayaks and a Paddleboard
Marathon, FL
- 10 Guests
- 4 Bedrooms
- 4 Bathrooms
Tipsy Turtle at Sombrero Beach ~ Fabulous 4 BR Private Pool Home
Marathon, FL
- 10 Guests
- 4 Bedrooms
- 3 Bathrooms
- Pets Allowed
Kon Tiki at Sombrero Beach ~ Waterfront vacation rental near Sombrero Beach
Marathon, FL
- 8 Guests
- 3 Bedrooms
- 2 Bathrooms
- Pets Allowed
Brisas Del Mar ~ Exclusive, Luxury Pool Home ~ Kayaks and Bikes included!
Marathon, FL
- 10 Guests
- 4 Bedrooms
- 5 Bathrooms
Salty Dog Villa ~ Villa with private pool ~ Hawks Cay on Duck Key
Duck Key, FL
- 10 Guests
- 4 Bedrooms
- 2.5 Bathrooms
Sombrero Serenity ~ Private Heated Pool
Marathon, FL
- 6 Guests
- 2 Bedrooms
- 2 Bathrooms
- Pets Allowed
Reel Therapy at Sombrero Beach ~ Fabulous Brand New 4 BR SINGLE Pool Home with kayaks
Marathon, FL
- 10 Guests
- 4 Bedrooms
- 3 Bathrooms
- Pets Allowed
Bird of Paradise ~ Gulf front rental with panoramic views
Marathon, FL
- 8 Guests
- 3 Bedrooms
- 3 Bathrooms
- Pets Allowed
Paradise Found ~ Large split level home with 5 kayaks and 4 bikes
Marathon, FL
- 12 Guests
- 5 Bedrooms
- 3 Bathrooms
- Pets Allowed
Sombrero Chic at Sombrero Beach ~ Beautiful 4 BR Attached Private Pool Home
Marathon, FL
- 10 Guests
- 4 Bedrooms
- 3 Bathrooms
- Pets Allowed
Private Oasis ~ Open Ocean Views!
Marathon, FL
- 10 Guests
- 4 Bedrooms
- 3 Bathrooms
- Pets Allowed
Vista Del Mar ~ Exclusive, luxury Pool Home
Marathon, FL
- 10 Guests
- 4 Bedrooms
- 4 Bathrooms
Reel Relaxin' ~ Florida Keys luxury 5 bedroom weekly vacation rental
Marathon, FL
- 12 Guests
- 5 Bedrooms
- 3.5 Bathrooms
- Pets Allowed
Reel Deal ~ Newly Remodeled ~ Quick Ocean Access ~ Room for 2 boats!
Marathon, FL
- 10 Guests
- 4 Bedrooms
- 3 Bathrooms
- Pets Allowed
Pier Pressure ~ 4 bedroom 4 bath single family pool home.
Marathon, FL
- 10 Guests
- 4 Bedrooms
- 4 Bathrooms
Getaway Bay at Coco Plum Beach ~ Private Pool Home
Marathon, FL
- 12 Guests
- 5 Bedrooms
- 4 Bathrooms
- Pets Allowed
Adventures in Paradise at Sombrero Beach ~ New pool home near beach with kayaks and boat dock!
Marathon, FL
- 10 Guests
- 4 Bedrooms
- 3 Bathrooms
- Pets Allowed
Casa Dulce at Sombrero Beach ~ single family home with heated pool and 60' dock
Marathon, FL
- 10 Guests
- 4 Bedrooms
- 3 Bathrooms
Paradise Cove at Sombrero Beach ~ Upscale Sombrero Beach vacation home with private pool!
Marathon, FL
- 10 Guests
- 4 Bedrooms
- 3.5 Bathrooms
- Pets Allowed
Cielos Del Mar 1 at Key Colony Beach ~ Rent both sides! Perfect for large groups
Key Colony Beach, FL
- 8 Guests
- 3 Bedrooms
- 3 Bathrooms
- Pets Allowed
Sunsets in Paradise ~ Open Gulf views
Marathon, FL
- 12 Guests
- 5 Bedrooms
- 3 Bathrooms
- Pets Allowed
Angler & Ale ~ Upscale Pool Home ~ Near The Beach
Marathon, FL
- 10 Guests
- 4 Bedrooms
- 3 Bathrooms
Three Sheets ~ Room for 2 boats!
Marathon, FL
- 10 Guests
- 4 Bedrooms
- 3 Bathrooms
- Pets Allowed
Cielos Del Mar 2 at Key Colony Beach ~ Rent both sides! Perfect for large groups
Key Colony Beach, FL
- 8 Guests
- 3 Bedrooms
- 3 Bathrooms
- Pets Allowed
Island Time - Luxury home seconds to the open Ocean
Marathon, FL
- 8 Guests
- 3 Bedrooms
- 2 Bathrooms
- Pets Allowed