Villas with a pool Florida Keys | Apartments to rent with swimming facilities

View larger map

Price per night

£194 Average

Price per night

to

Bedrooms

Bathrooms

Location

  • United States
  • Florida
  • Florida Keys

Location

  • All locations
  • Cudjoe Key (4)
  • Duck Key (1)
  • Islamorada (46)
  • Key Colony Beach (5)
  • Key Largo (37)
  • Key West (36)
  • Long Key (2)
  • Marathon (18)
  • Matecumbe Key (1)

More

Less

Also consider

Villas Key Largo
122 properties
Holiday rentals Islamorada
69 properties
Villas Key West
69 properties
Estates Marathon
48 properties
Big Pine Key
11 properties
Key Colony Beach
8 properties
Cudjoe Key
7 properties
Long Key
6 properties
Payment Protection
To book this holiday home you need to pay through the Holiday Lettings website. We can’t protect your payment if you don’t pay through us. Learn more

151 Holiday homes

Filters applied: Swimming pool (151)

Travellers going to Florida Keys are booking March dates now. Secure your holiday home today and have the perfect trip.

(3) Very Good 

1 / 5

Holiday apartment with shared pool in Key West

Florida Keys / Key West

2 6 Min stay varies

Apartment / 2 bedrooms / sleeps 6 / Min stay varies

Add to shortlist

from £204 / night

£1425 - £1497 / week

Book

from £204 / night

(8) Very Good 

1 / 14

Holiday apartment in Key West

Florida Keys / Key West

3 6 Min stay varies

Apartment / 3 bedrooms / sleeps 6 / Min stay varies

Add to shortlist

from £311 / night

£2173 - £2897 / week

Book

from £311 / night

(20) Very Good 

1 / 14

Apartment rental in Key West

Florida Keys / Key West

3 8 Min stay varies

Apartment / 3 bedrooms / sleeps 8 / Min stay varies

Add to shortlist

from £207 / night

£1589 - £1734 / week

Book

from £207 / night

(3) Excellent 

1 / 15

Apartment rental in Key West

Florida Keys / Key West

2 4 7 nights min stay

Apartment / 2 bedrooms / sleeps 4 / 7 nights min stay

Add to shortlist

from £187 / night

£1294 / week

Book

from £187 / night

(6) Excellent 

1 / 19

Villa rental in Islamorada

Florida Keys / Islamorada

2 6 7 nights min stay

Villa / 2 bedrooms / sleeps 6 / 7 nights min stay

Add to shortlist

from £178 / night

£1242 - £1725 / week

Book

from £178 / night

(9) Very Good 

1 / 12

Holiday apartment in Key West

Florida Keys / Key West

2 5 Min stay varies

Apartment / 2 bedrooms / sleeps 5 / Min stay varies

Add to shortlist

from £121 / night

£828 - £1725 / week

Book

from £121 / night

(16) Excellent 

1 / 17

Key West holiday apartment let

Florida Keys / Key West

2 5 Min stay varies

Apartment / 2 bedrooms / sleeps 5 / Min stay varies

Add to shortlist

from £172 / night

£1203 / week

Book

from £172 / night

(2) Excellent 

1 / 20

Islamorada holiday condo rental

Florida Keys / Islamorada

3 8 Min stay varies

Condo / 3 bedrooms / sleeps 8 / Min stay varies

Add to shortlist

from £173 / night

£1035 - £2414 / week

Book

from £173 / night

1 / 24

Holiday home in Key West

Florida Keys / Key West

2 5 30 nights min stay

House / 2 bedrooms / sleeps 5 / 30 nights min stay

Add to shortlist

from £248 / night

£1730 / week

Book

from £248 / night

1 / 24

Holiday condo in Islamorada

Florida Keys / Islamorada

2 6 7 nights min stay

Condo / 2 bedrooms / sleeps 6 / 7 nights min stay

Add to shortlist

from £173 / night

£1207 - £2069 / week

Book

from £173 / night

(22) Excellent 

1 / 29

Holiday home in Islamorada

Florida Keys / Islamorada

2 5 7 nights min stay

House / 2 bedrooms / sleeps 5 / 7 nights min stay

Add to shortlist

from £193 / night

£1345 - £1552 / week

Book

from £193 / night

(2) Very Good 

1 / 25

Holiday apartment in Islamorada

Florida Keys / Islamorada

2 4 7 nights min stay

Apartment / 2 bedrooms / sleeps 4 / 7 nights min stay

Add to shortlist

from £173 / night

£1069 / week

Book

from £173 / night

(3) Excellent 

1 / 37

Holiday home with swimming pool in Key Largo

Florida Keys / Key Largo

3 8 Min stay varies

House / 3 bedrooms / sleeps 8 / Min stay varies

Add to shortlist

from £552 / night

£5173 - £5518 / week

Book

from £552 / night

(1) Excellent 

1 / 9

Islamorada holiday condo rental

Florida Keys / Islamorada

2 50 7 nights min stay

Condo / 2 bedrooms / sleeps 50 / 7 nights min stay

Add to shortlist

from £976 / night

£6827 / week

Book

from £976 / night

(1) Excellent 

1 / 26

Cudjoe Key holiday home rental

Florida Keys / Cudjoe Key

2 6 Min stay varies

House / 2 bedrooms / sleeps 6 / Min stay varies

Add to shortlist

from £163 / night

£1104 - £1242 / week

Book

from £163 / night

(2) Excellent 

1 / 9

Holiday apartment in Key Largo

Florida Keys / Key Largo

2 6 2 nights min stay

Apartment / 2 bedrooms / sleeps 6 / 2 nights min stay

Add to shortlist

from £163 / night

£966 / week

Book

from £163 / night

(4) Excellent 

1 / 12

Holiday villa in Marathon

Florida Keys / Marathon

3 6 7 nights min stay

Villa / 3 bedrooms / sleeps 6 / 7 nights min stay

Add to shortlist

from £217 / night

£1518 - £2069 / week

Book

from £217 / night

1 / 26

Holiday cottage with swimming pool in Islamorada

Florida Keys / Islamorada

2 6 30 nights min stay

Cottage / 2 bedrooms / sleeps 6 / 30 nights min stay

Add to shortlist

from £121 / night

£845 / week

Book

from £121 / night

(5) Excellent 

1 / 40

Holiday home rental

Florida Keys / Islamorada

3 6 Min stay varies

House / 3 bedrooms / sleeps 6 / Min stay varies

Add to shortlist

from £178 / night

£1242 - £1725 / week

Book

from £178 / night

1 / 25

Villa rental in Islamorada

Florida Keys / Islamorada

2 6 7 nights min stay

Villa / 2 bedrooms / sleeps 6 / 7 nights min stay

Add to shortlist

from £193 / night

£1207 - £1518 / week

Book

from £193 / night

(2) Very Good 

1 / 14

Key Largo holiday condo rental

Florida Keys / Key Largo

2 6 Min stay varies

Condo / 2 bedrooms / sleeps 6 / Min stay varies

Add to shortlist

from £121 / night

£794 - £1156 / week

Book

from £121 / night

1 / 22

Holiday condo in Key West

Florida Keys / Key West

2 6 Min stay varies

Condo / 2 bedrooms / sleeps 6 / Min stay varies

Add to shortlist

from £156 / night

£1104 - £1725 / week

Book

from £156 / night

1 / 32

Holiday yacht rental

Florida Keys / Key West

2 4 1 night min stay

Yacht / 2 bedrooms / sleeps 4 / 1 night min stay

Add to shortlist

from £276 / night

£1932 / week

Book

from £276 / night

(4) Very Good 

1 / 20

Holiday apartment in Key West

Florida Keys / Key West

2 6 Min stay varies

Apartment / 2 bedrooms / sleeps 6 / Min stay varies

Add to shortlist

from £166 / night

£1104 - £1276 / week

Book

from £166 / night

1 / 10

Holiday home in Islamorada

Florida Keys / Islamorada

4 8 30 nights min stay

House / 4 bedrooms / sleeps 8 / 30 nights min stay

Add to shortlist

from £296 / night

£2069 / week

Book

from £296 / night

1 / 28

Holiday home in Key West

Florida Keys / Key West

3 6 30 nights min stay

House / 3 bedrooms / sleeps 6 / 30 nights min stay

Add to shortlist

from £207 / night

£1444 / week

Book

from £207 / night

(3) Very Good 

1 / 6

Home rental in Key Largo with shared pool

Florida Keys / Key Largo

1 4 Min stay varies

House / 1 bedroom / sleeps 4 / Min stay varies

Add to shortlist

from £145 / night

£1051 / week

Book

from £145 / night

1 / 25

Holiday home accommodation

Florida Keys / Islamorada

2 6 Min stay varies

House / 2 bedrooms / sleeps 6 / Min stay varies

Add to shortlist

from £1380 / night

£1380 - £5173 / week

Book

from £1380 / night

1 / 14

Holiday home in Islamorada

Florida Keys / Islamorada

2 6 7 nights min stay

House / 2 bedrooms / sleeps 6 / 7 nights min stay

Add to shortlist

from £158 / night

£1103 - £2069 / week

Book

from £158 / night

1 / 21

Apartment rental in Islamorada with tennis court

Florida Keys / Islamorada

3 6 7 nights min stay

Apartment / 3 bedrooms / sleeps 6 / 7 nights min stay

Add to shortlist

from £217 / night

£1518 - £2414 / week

Book

from £217 / night

(2) Excellent 

1 / 30

Holiday condo in Key West

Florida Keys / Key West

2 5 Min stay varies

Condo / 2 bedrooms / sleeps 5 / Min stay varies

Add to shortlist

from £280 / night

£1552 - £2242 / week

Book

from £280 / night

(1) Excellent 

1 / 19

Key West holiday home rental

Florida Keys / Key West

3 8 30 nights min stay

House / 3 bedrooms / sleeps 8 / 30 nights min stay

Add to shortlist

from £115 / night

£805 / week

Book

from £115 / night

1 / 18

Condo rental in Key West with golf nearby

Florida Keys / Key West

3 9 30 nights min stay

Condo / 3 bedrooms / sleeps 9 / 30 nights min stay

Add to shortlist

from £160 / night

£1119 / week

Book

from £160 / night

(7) Excellent 

1 / 15

Holiday apartment with tennis court in Marathon

Florida Keys / Marathon

3 8 Min stay varies

Apartment / 3 bedrooms / sleeps 8 / Min stay varies

Add to shortlist

from £166 / night

£1104 - £1449 / week

Book

from £166 / night

(2) Excellent 

1 / 9

Islamorada holiday b&b rental

Florida Keys / Islamorada

1 2 1 night min stay

B&B / 1 bedroom / sleeps 2 / 1 night min stay

Add to shortlist

from £89 / night

£623 / week

Book

from £89 / night

1 / 9

Holiday apartment in Islamorada

Florida Keys / Islamorada

2 4 Min stay varies

Apartment / 2 bedrooms / sleeps 4 / Min stay varies

Add to shortlist

from £104 / night

£725 / week

Book

from £104 / night

(1) Very Good 

1 / 17

Holiday condo with shared pool in Key West

Florida Keys / Key West

2 6 7 nights min stay

Condo / 2 bedrooms / sleeps 6 / 7 nights min stay

Add to shortlist

from £247 / night

£1725 / week

Book

from £247 / night

1 / 30

Holiday apartment with swimming pool, tennis court in Islamorada

Florida Keys / Islamorada

3 8 30 nights min stay

Apartment / 3 bedrooms / sleeps 8 / 30 nights min stay

Add to shortlist

from £83 / night

£580 / week

Book

from £83 / night

1 / 7

Holiday condo in Key Largo

Florida Keys / Key Largo

2 8 3 nights min stay

Condo / 2 bedrooms / sleeps 8 / 3 nights min stay

Add to shortlist

from £173 / night

£1087 / week

Book

from £173 / night

1 / 34

Holiday home in Islamorada

Florida Keys / Islamorada

4 10 30 nights min stay

House / 4 bedrooms / sleeps 10 / 30 nights min stay

Add to shortlist

from £575 / night

£4023 / week

Book

from £575 / night

1 / 13

Condo rental in Islamorada

Florida Keys / Islamorada

2 6 7 nights min stay

Condo / 2 bedrooms / sleeps 6 / 7 nights min stay

Add to shortlist

from £98 / night

£686 / week

Book

from £98 / night

1 / 17

Holiday home in Marathon

Florida Keys / Marathon

2 6 7 nights min stay

House / 2 bedrooms / sleeps 6 / 7 nights min stay

Add to shortlist

from £242 / night

£1380 - £1932 / week

Book

from £242 / night

1 / 4

Holiday condo in Key West

Florida Keys / Key West

2 6 7 nights min stay

Condo / 2 bedrooms / sleeps 6 / 7 nights min stay

Add to shortlist

from £158 / night

£1104 / week

Book

from £158 / night

(2) Excellent 

1 / 41

Holiday apartment in Florida Keys

Florida / Florida Keys

2 4 7 nights min stay

Apartment / 2 bedrooms / sleeps 4 / 7 nights min stay

Add to shortlist

from £137 / night

£956 / week

Book

from £137 / night

1 / 29

Key Largo holiday villa rental

Florida Keys / Key Largo

2 6 Min stay varies

Villa / 2 bedrooms / sleeps 6 / Min stay varies

Add to shortlist

from £121 / night

£621 - £1035 / week

Book

from £121 / night

(1) Excellent 

1 / 19

Condo rental in Islamorada

Florida Keys / Islamorada

1 4 7 nights min stay

Condo / 1 bedroom / sleeps 4 / 7 nights min stay

Add to shortlist

from £138 / night

£569 - £673 / week

Book

from £138 / night

1 / 25

Holiday apartment rental

Florida Keys / Key Largo

2 6 4 nights min stay

Apartment / 2 bedrooms / sleeps 6 / 4 nights min stay

Add to shortlist

from £173 / night

£1000 / week

Book

from £173 / night

(2) Very Good 

1 / 31

Holiday apartment in Key Largo

Florida Keys / Key Largo

3 6 7 nights min stay

Apartment / 3 bedrooms / sleeps 6 / 7 nights min stay

Add to shortlist

from £135 / night

£942 / week

Book

from £135 / night

(5) Excellent 

1 / 31

Holiday home rental

Florida Keys / Marathon

4 10 7 nights min stay

House / 4 bedrooms / sleeps 10 / 7 nights min stay

Add to shortlist

from £370 / night

£2587 - £3621 / week

Book

from £370 / night

1 / 17

Villa accommodation in Marathon with golf nearby

Florida Keys / Marathon

3 8 Min stay varies

Villa / 3 bedrooms / sleeps 8 / Min stay varies

Add to shortlist

from £190 / night

£1328 / week

Book

from £190 / night

Don’t let an old browser slow down your holiday

Your browser is out of date and might not work well with our website. Download the latest version to speed up your hunt for the perfect holiday home.

Just click on the icons to get to the download page