Villas with a pool North America | Apartments to rent with swimming facilities | Holiday Lettings

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65,361 Holiday homes

Filters applied: Swimming pool

(26) Excellent 

24

Holiday villa with swimming pool in Willikies

Willikies / The Peninsula

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 2 km
  • Swimming pool
“A fantastic place just what we needed” We stayed here as a couple in June 2016. This is the off season on the Island and it is very quiet and a lot of the restaurants are closed, but this is exactly what we needed as you get to experience the island w
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from £171 / night

£1200 - £2600 / week

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from £171 / night

(13) Excellent 

36

Holiday villa with swimming pool, golf nearby in Saint Mary's

Antigua / Saint Mary's

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £250 / night

£1750 - £2780 / week

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from £250 / night

(17) Excellent 

15

Orlando holiday villa rental

Central Florida / Orlando

5 12 7 nights min

  • 5 bedrooms
  • Sleeps 12
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Wow!! Beautiful well equipped villa” We had a lovely stay at the Orlando Sky Villa for 3 weeks. Great location, beautifully kept villa and pool area. Very well equipped and clean.
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from £79 / night

£550 - £680 / week

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from £79 / night

(3) Excellent 

23

Old Town holiday townhouse rental

Florida / Old Town

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £60 / night

£420 - £630 / week

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from £60 / night

(13) Excellent 

50

Holiday villa letting

Central Florida / Orlando

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 125 km
  • Swimming pool
  • Child friendly
“perfect holiday, would definately come again” We have just returned from a 2 week holiday in Weston Magic. The location is perfect and all the attractions are within easy reach by car. The home is the perfect place to relax and has everything you ne
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from £80 / night

£560 / week

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from £80 / night

(2) Excellent 

91

Villa accommodation in Kissimmee

Kissimmee / Kissimmee City

5 10 6 nights min

  • 5 bedrooms
  • Sleeps 10
  • 6 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £129 / night

£903 / week

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from £129 / night

(5) Very Good 

37

Villa rental in Jolly Harbour with shared pool, golf nearby

Saint Mary Parish / Jolly Harbour

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“NICE AND QUIET PLACE” We stayed almost two months in the villa and really appreciate it. The villa is very clean and updated. We specially appreciated having all our meals outside looking at the very nice view. The extended deck is fantastic and th
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from £104 / night

£727 / week

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from £104 / night

(2) Excellent 

20

Boynton Beach holiday villa rental

Florida / Boynton Beach

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 5 km
  • Swimming pool

from £154 / night

£770 - £1154 / week

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from £154 / night

(2) Excellent 

26

Holiday villa in Siesta Key

Florida / Siesta Key

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £160 / night

£820 - £1520 / week

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from £160 / night

(17) Very Good 

42

Palm Harbor holiday apartment rental

Florida / Palm Harbor

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 5 km
  • Swimming pool
“Lovely villa, home from home” Just returned today fromTarpon Springs, The villa is a lovely size and has all the amenties required for a relaxing stay. The rooms are very big and the balcony has a very pleasant view of the marina. Head out in the suns
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from £70 / night

£395 / week

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from £70 / night

(21) Excellent 

24

Holiday villa in Fort Myers Beach

Southwest Gulf Coast / Fort Myers Beach

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £176 / night

£1227 - £1704 / week

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from £176 / night

(2) Excellent 

19

Villa rental in Saint Francois with swimming pool, golf nearby

Grande-Terre Island / Saint Francois

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Swimming pool

from £136 / night

£949 - £1199 / week

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from £136 / night

(19) Very Good 

Certificate of Excellence

18

Holiday bungalow with shared pool in Sainte-Anne

Grande-Terre Island / Sainte-Anne

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 2 km
  • Swimming pool
“Can't find anything to fault” This is a lovely bungalow set within mango and starfruit trees. It is well equipped and the pool is within the grounds. The owners, Christine and Jean-Marc are friendly and helpful without being intrusive. When the a
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Certificate of Excellence

from £35 / night

£242 - £393 / week

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from £35 / night

(4) Excellent 

21

Bungalow rental in Sainte-Anne with shared pool

Grande-Terre Island / Sainte-Anne

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £65 / night

£432 / week

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from £65 / night

(23) Excellent 

16

Orlando holiday villa rental

Orlando / Westridge

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Oasis away from but close to Disney World” We were looking for a home away from home for our 3 week trip to Disney and other parks in the Orlando region and found the perfect holiday home. The house was an easy 20 minute drive from the Magic Kingdom o
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from £97 / night

£630 - £700 / week

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from £97 / night

(5) Excellent 

28

Holiday condo in Anna Maria Island

Florida / Anna Maria Island

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £85 / night

£590 - £1380 / week

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from £85 / night

(20) Excellent 

20

Home rental in Maynards with swimming pool

Saint Peter Parish / Maynards

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Swimming pool
“Lovely Villa, great location” Our party of family and friends had a lovely time at Palm Villa. The facilities are excellent, it was plenty big enough for all ten of us and Beverley was helpful and went out of her way to make our stay comfortable. We
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from £125 / night

£875 - £2555 / week

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from £125 / night

(19) Excellent 

24

Holiday villa rental with swimming pool

Lake County / Clermont

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 130 km
  • Swimming pool
“Fabulous Excellent Gorgeous” We stayed at Orange Tree Retreat for 2 weeks and it was absolutely brilliant. Great Villa, fabulous location, home from home - loved every minute of our stay. This villa offers everything you could possibly want - it is
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from £66 / night

£539 - £693 / week

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from £66 / night

(23) Excellent 

23

Holiday villa in Orlando

Orlando / Orange Tree

4 8 5 nights min

  • 4 bedrooms
  • Sleeps 8
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Firefighter rated as best place to stay in Disney area for house rentals” Just wanted to pass along some great reviews for this house rental. Stayed as a group of adult softball players from NH attending ESPN tournament at Disney in December. This hou
…see more

from £146 / night

£985 - £1224 / week

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from £146 / night

(23) Very Good 

22

Villa rental in Orlando

Central Florida / Orlando

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 80 km
  • Swimming pool
“Very Nice.” We booked this house as a last minute get away for a week (10-17 June 2013). Excellent value – a lot of house for the money! It was well presented and clean when we arrived – with plenty of towels etc (you do need your own pool towels).
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from £138 / night

£960 / week

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from £138 / night

(42) Excellent 

31

Holiday villa rental

Haines City / Calabay Parc at Tower Lake

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 50 km
  • Swimming pool
“Perfect Villa, perfect owner, holiday of a life time. 'Dreams come true!'” Julie, We would like to take this opportunity to thank you for the help and advice you provided us from the moment we first contacted you to enquire about renting your villa
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from £95 / night

£665 / week

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from £95 / night

(5) Very Good 

20

Holetown holiday apartment rental

Saint James Parish / Holetown

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Air conditioning

from £75 / night

£525 - £805 / week

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from £75 / night

(56) Excellent 

60

Villa rental in Kissimmee

Kissimmee / Indian Ridge

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Couldn't be anywhere better to stay” As the holiday season is a time for family we decided to have a mini family reunion and renting this Villa was the best thing we did. We were able to cook, use the pool and the kids were always entertain. The house
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from £90 / night

£475 - £725 / week

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from £90 / night

24

Holiday windmill letting

Cape Cod / Centerville

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Swimming pool

from £958 / night

£6700 / week

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from £958 / night

(24) Excellent 

17

Holiday townhouse with swimming pool in Holetown

Saint James Parish / Holetown

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Swimming pool
“If you really want to feel at home on holiday, look no further.” After a fantastic stay last year we returned here for 2 weeks in April/May (this time 5 of us). Yet again despite its size and very modern feel we immediately felt at home – definitely a
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from £280 / night

£1960 - £3990 / week

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from £280 / night

(44) Excellent 

27

Holiday villa with swimming pool in Davenport

Central Florida / Orlando

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 80 km
  • Swimming pool

from £95 / night

£630 - £725 / week

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from £95 / night

(2) Excellent 

22

Davenport holiday villa rental

Davenport / Watersong Resort

5 14 Min stay varies

  • 5 bedrooms
  • Sleeps 14
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £100 / night

£700 - £1200 / week

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from £100 / night

(4) Excellent 

29

Holiday condo with shared pool in Seven Mile Beach

Grand Cayman / Seven Mile Beach

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Swimming pool

from £662 / night

£7847 - £11924 / week

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from £662 / night

(46) Excellent 

41

Orlando holiday villa rental

Orlando / Orange Tree

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Nearest beach 127 km
  • Swimming pool
  • Child friendly
“Super Villa” We have just returned from our holiday in Orlando staying in a Villa supplied by Floridavillabookers in Orange Tree. The owner Yvonne Robinson is most pleasant and friendly to deal with by keeping you informed of all you need from you bo
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from £93 / night

£650 - £745 / week

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from £93 / night

(15) Very Good 

25

Holiday villa in Cape Coral

Southwest Gulf Coast / Cape Coral

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 15 km
  • Swimming pool

from £108 / night

£754 - £1000 / week

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from £108 / night

(10) Excellent 

20

Holiday villa with shared pool in Saint Anne

Guadeloupe / Saint Anne

4 10 7 nights min

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Swimming pool

from £271 / night

£1897 - £5095 / week

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from £271 / night

(7) Very Good 

23

Holiday villa with swimming pool in Weston

Saint James Parish / Weston

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Definitely the place to stay.” We spent an amazing, relaxing week at this beautiful beach villa in St. James. The house is tucked away behind an electronic gate down a private drive. The beach is on your door step and the views from the veranda are br
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from £616 / night

£4308 / week

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from £616 / night

(12) Very Good 

28

Villa rental in Naples with golf nearby

Naples / Lely Resort

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 13 km
  • Swimming pool

from £127 / night

£885 - £1424 / week

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from £127 / night

(23) Very Good 

39

Davenport holiday villa rental

Davenport / Lake Wilson Preserve

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly
“Great house” Superb, handy location, close to everything. The private heated pool was brilliant, nice and relaxing. A nice quiet area, tucked out of the way.
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from £57 / night

£399 - £545 / week

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from £57 / night

(27) Excellent 

24

Holiday condo with golf nearby in Orlando

Orlando / Vista Cay

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 90 km
  • Swimming pool
  • Child friendly
“Excellent accomodation” Just returned this morning from staying in townhouse isles at cay common and having been in Orlando 4 times found location of apartment,facilities & apartment well equipped. publix supermarket and food restaurants next door.loc
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from £66 / night

£462 - £504 / week

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from £66 / night

(19) Excellent 

16

Studio rental in Sainte-Luce with shared pool

Arrondissement of Le Marin / Sainte-Luce

Studio 2 7 nights min

  • Studio
  • Sleeps 2
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Air conditioning

from £52 / night

£302 - £345 / week

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from £52 / night

(10) Excellent 

29

Villa rental in Las Galeras with swimming pool

Samana Province / Las Galeras

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 3 km
  • Swimming pool

from £116 / night

£582 - £1454 / week

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from £116 / night

(13) Excellent 

20

Villa rental in Davenport with golf nearby

Central Florida / Davenport

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 130 km
  • Swimming pool
  • Child friendly
“What you see is exactly what you get” This villa is totally amazing there was 6 of us and had plenty room.the villa could not be faulted in any way it was exactly how it was described. Thank you so much for allowing us to stay in your beautiful villa
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from £70 / night

£485 - £717 / week

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from £70 / night

(21) Very Good 

23

Holiday townhouse with shared pool in Fitts

Saint James Parish / Fitts

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.25 km
  • Swimming pool
“Perfect family friendly villa” Ajoupa villa is set in a quiet and peaceful location, with easy access to the nearby beach and restaurants. The pool was a great place to cool off in after days spent on the beach. Their was a welcome pack on arrival whi
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from £70 / night

£490 - £590 / week

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from £70 / night

(18) Excellent 

20

Castara holiday villa rental

Castara / Englishman's Bay

5 8 Min stay varies

  • 5 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Swimming pool
“Very peaceful and spacious home in a great location.” Everything was well prepared when we arrived. Jango (the master gardener and our greeter when we arrived) was very patient and waited for 4 hours as our flight was delayed. The house was well equi
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from £114 / night

£800 - £1450 / week

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from £114 / night

1