Watersports holiday villas and apartments Florida | Holiday Lettings

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4,185 Holiday homes

Filters applied: Water sports

(2) Excellent 

10

Holiday villa letting

Rotonda West / Long Meadow

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 7 km
  • Swimming pool

from £85 / night

£595 - £1150 / week

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Responds fast!
avg. 3 hours 23 minutes

from £85 / night

(11) Excellent 

18

Holiday home in Orlando

Central Florida / Orlando

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Even better than expected.” We just had 2 weeks at this amazing house with ages ranging from 18 up to 50s. . I can't fault it in anyway. The owner Valerie was so helpful at the time of booking and the people that looked after the house were also ver
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from £75 / night

£575 - £875 / week

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Responds fast!
avg. 3 hours 38 minutes

from £75 / night

(2) Very Good 

10

Holiday home in Matlacha

Florida / Matlacha

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Suitable for children age 5+

from £54 / night

£354 - £708 / week

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Responds fast!
avg. 3 hours 35 minutes

from £54 / night

(7) Average 

36

Holiday apartment with swimming pool, golf nearby in Florida

Florida / Miami Beach

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £143 / night

£913 - £1374 / week

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from £143 / night

26

Condo rental in Little Gasparilla Island

Southwest Gulf Coast / Little Gasparilla Island

2 4 Min stay varies

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

from £112 / night

£794 - £1032 / week

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Responds fast!
avg. 2 hours 34 minutes

from £112 / night

(9) Excellent 

19

Holiday villa in Orlando

Central Florida / Orlando

4 8 Min stay varies

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

from £88 / night

£596 - £790 / week

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from £88 / night

(5) Very Good 

19

Holiday bungalow in Clermont

Clermont / High Grove

4 10 4 nights min

  • 4 bedrooms
  • Sleeps 10
  • 4 nights min
  • Beach / lakeside relaxation
  • Nearest beach 60 km
  • Swimming pool

from £100 / night

£550 / week

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Responds fast!
avg. 1 hour 11 minutes

from £100 / night

(6) Very Good 

67

Holiday home in Florida

Florida / Miami

3 6 Min stay varies

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

from £278 / night

£1429 - £2381 / week

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Responds fast!
avg. 1 hour 59 minutes

from £278 / night

(5) Very Good 

26

Holiday villa rental

Central Florida / Orlando

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Charming villa in excellent location” The villa is located away from the hustle and bustle of Orlando but is near enough to the theme parks and local shops to be convenient. The gated community gives a feeling of safety and has some excellent faciliti
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from £135 / night

£945 - £1330 / week

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from £135 / night

31

Holiday apartment with swimming pool, golf nearby in Florida

Florida / Miami Beach

3 8 Min stay varies

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

from £262 / night

£1580 - £2040 / week

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from £262 / night

(11) Excellent 

18

Holiday villa with golf nearby in Estero

Southwest Gulf Coast / Estero

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 10 km
  • Swimming pool
“Great Location” Had the opportunity to find this lovely villa at short notice. Was not disappointed. Adrian ensured everything was in place for arrival complete with directions. In all we spent about 4 weeks in this lovely home from home. Really miss
…see more

from £93 / night

£650 - £750 / week

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from £93 / night

(10) Excellent 

31

Holiday villa with swimming pool, golf nearby in Haines City

Haines City / Calabay Parc at Tower Lake

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Cracking villa, going back next year” This villa is set in a gated community and is very safe and peaceful. It's a great base to get to all theme parks within 1/2 hour depending on the traffic. You have a walmart and Winn dixies only 5 minutes drive a
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from £100 / night

£695 - £950 / week

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from £100 / night

(5) Excellent 

15

Davenport holiday villa rental

Davenport / Sandy Ridge

5 8 7 nights min

  • 5 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £75 / night

£525 - £715 / week

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from £75 / night

(4) Excellent 

24

Holiday villa with swimming pool, golf nearby in Port Charlotte

Southwest Gulf Coast / Port Charlotte

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 25 km
  • Swimming pool

from £56 / night

£391 / week

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Responds fast!
avg. 3 hours 35 minutes

from £56 / night

(13) Very Good 

Certificate of Excellence

47

Holiday townhouse with shared pool, golf nearby in Davenport

Davenport / Regal Palms

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 130 km
  • Swimming pool
“Great stay and very helpful home owner!” We had a great stay here! Before we booked and before our arrival we had a few questions as we were traveling with a 1 year old and a 2 year old. Quick and accommodating responses put us at ease. The house and
…see more

Certificate of Excellence

from £75 / night

£520 / week

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from £75 / night

(8) Excellent 

18

Holiday home in Bradenton

Bradenton / Sabal Harbour

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £100 / night

£650 / week

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Responds fast!
avg. 2 hours 3 minutes

from £100 / night

(26) Very Good 

25

Holiday home in Kissimmee

Central Florida / Kissimmee

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Just Perfect” My wife and I are regular visitors to the Orlando area and have stayed in several Rental Villas in the past. It was our first time at ‘Ventura Villa’ hopefully not our last, we had a really enjoyable stay. The villa is clean, well fur
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from £80 / night

£525 - £1054 / week

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from £80 / night

(21) Excellent 

24

Haines City holiday villa rental

Haines City / Calabay Parc at Tower Lake

4 8 4 nights min

  • 4 bedrooms
  • Sleeps 8
  • 4 nights min
  • Beach / lakeside relaxation
  • Nearest beach 80 km
  • Swimming pool
“Wonderful Holiday” We thoroughly enjoyed our stay in this villa. It was beautifully clean & well presented, somewhere to really relax after being out at the theme parks all day. It was handy for a choice of supermarkets & filling stations as well as
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from £100 / night

£600 / week

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from £100 / night

23

Holiday home in Port Charlotte

Southwest Gulf Coast / Port Charlotte

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 8 km
  • Swimming pool

from £67 / night

£400 - £681 / week

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from £67 / night

(10) Excellent 

24

Holiday home in Kissimmee

Kissimmee / Tuscany, Florida

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
“Wonderful holiday in a fantastic Villa!” This was our second family holiday to Orlando so we had an idea of what we were looking for from a villa and a location close to the parks. We considered a number of possible options before settling on Luce Del
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from £115 / night

£805 - £980 / week

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from £115 / night

(8) Very Good 

30

Fort Myers Beach holiday home let

Fort Myers Beach / Estero Island

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Swimming pool

from £238 / night

£1587 - £2381 / week

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from £238 / night

(28) Excellent 

24

Englewood holiday villa rental with swimming pool

Southwest Gulf Coast / Rotonda West

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 5 km
  • Swimming pool
“A real home from home!” Often said but very true. This property had everything we needed and extremely well maintained since our first visit 3 years ago. Although there were only 2 of us it is perfect for a larger family or group of friends with a gre
…see more

from £69 / night

£500 - £550 / week

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from £69 / night

(12) Very Good 

24

Kissimmee holiday villa rental

Kissimmee / Cumbrian Lakes

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Great Villa for families” We stayed at this villa with our daughter and my wife's parents. This is a fantastic property for more than one family as there are two master suites as well as a queen room and two twin bedrooms. The best feature is the exte
…see more

from £100 / night

£550 - £700 / week

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from £100 / night

(4) Very Good 

60

Holiday apartment with shared pool in Sunny Isles Beach

Florida / Sunny Isles Beach

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £104 / night

£723 / week

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from £104 / night

(2) Excellent 

36

Holiday home rental

Southwest Gulf Coast / Captiva Island

5 8 7 nights min

  • 5 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Swimming pool

from £339 / night

£2372 - £4237 / week

Enquire View

from £339 / night

(6) Excellent 

48

Clermont holiday villa rental

Clermont / Clear Creek

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
“Great holiday” Stayed for two weeks, nice neighborhood, good restaurants and shopping nearby. Nice clean house, nice to have the pond right next to the house. Sad about the pool heating (375$), it wasn't warm even though we put the cover on every nigh
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from £68 / night

£473 / week

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Responds fast!
avg. 2 hours 15 minutes

from £68 / night

(23) Excellent 

22

Holiday villa with swimming pool in Kissimmee

Kissimmee / Bellavida Resort

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Perfect villa for all the Orlando attractions” Belles Cove is a lovely family home and ideally located for the parks and other attractions The rooms are tastefully decorated and with the benefit of 4 bathrooms presents ideal accommodation for a large
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from £105 / night

£635 - £825 / week

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Responds fast!
avg. 3 hours 45 minutes

from £105 / night

(11) Excellent 

22

Davenport holiday villa rental

Davenport / Watersong Resort

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 80 km
  • Swimming pool

from £124 / night

£917 - £1367 / week

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from £124 / night

(8) Excellent 

21

Kissimmee holiday home rental

Kissimmee / Trafalgar Village

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 50 km
  • Swimming pool
“Fabulous home away from home” Ten of us stayed in this Villa, consisting 3 children, 2 teenagers and 5 adults. We had plenty of room for all of us as it's such a large property. The Villa was very well equipped with everything we needed and spotlessly
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from £120 / night

£917 / week

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Responds fast!
avg. 3 hours 38 minutes

from £120 / night

(2) Very Good 

34

Holiday home with swimming pool in Florida

Florida / Sunny Isles Beach

4 12 2 nights min

  • 4 bedrooms
  • Sleeps 12
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.3 km
  • Swimming pool

from £198 / night

£1429 / week

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from £198 / night

(27) Excellent 

24

Holiday villa in Rotonda West

Rotonda West / Rotonda Lakes

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 10 km
  • Swimming pool
“Great Villa” We have just returned after 2 weeks in this lovely Villa,it i so quiet and peaceful,with lots off places to explore nearby. It has everything that you need for a great holiday.The pool was well used as it was very hot,although we had Stor
…see more

from £85 / night

£495 - £650 / week

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from £85 / night

(1) Excellent 

11

Holiday home with swimming pool, golf nearby in Sebastian

Florida / Sebastian

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Great house and flying holiday” We had the house for a week and 2x PA28s based at Sebastian Airport. The house is fantastic - spacious, clean, comfy, lovely swimming pool. It's on a very quiet private road with no through-traffic. The airport's just a
…see more

from £171 / night

£1191 / week

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from £171 / night

(14) Very Good 

24

Home rental in Fort Myers with golf nearby

Fort Myers / South Fort Myers

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 25 km
  • Swimming pool
“Great Southwest Florida Destination!!” Our family of five recently returned from a 10 day stay at this home. The home is in a quiet neighborhood, very convenient to the airport, Highway 75, shopping and golf courses. The home is beautifully decorate
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from £72 / night

£500 - £790 / week

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from £72 / night

(3) Excellent 

29

Four Corners holiday villa rental

Central Florida / Four Corners

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £80 / night

£550 - £1210 / week

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Responds fast!
avg. 3 hours 25 minutes

from £80 / night

(14) Very Good 

Certificate of Excellence

15

Orlando holiday villa rental

Central Florida / Orlando

4 8 5 nights min

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

Certificate of Excellence

from £90 / night

£490 - £595 / week

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Responds fast!
avg. 1 hour 58 minutes

from £90 / night

(14) Excellent 

24

Kissimmee holiday villa rental

Kissimmee / Veranda Palms

4 8 4 nights min

  • 4 bedrooms
  • Sleeps 8
  • 4 nights min
  • Beach / lakeside relaxation
  • Nearest beach 75 km
  • Swimming pool
“Lovely villa, great service and excellent location for all the Disney parks!” Definitely recommended! From the moment I enquired about the villa, (we dealt directly with the owner) we received excellent service. Booking was easy, and we were supplie
…see more

from £90 / night

£580 - £775 / week

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from £90 / night

(7) Very Good 

12

Holiday villa with golf nearby in Fort Myers

Fort Myers / South Fort Myers

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 10 km
  • Swimming pool
“Great place” Really enjoyed our stay, enjoyed the villa. Management company where excellent, providing an excellent prompt service when a smoke alarm decided it's battery was low and kept on bleeping.(really annoying!). My only gripe was that a bbq wa
…see more

from £103 / night

£715 - £1016 / week

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from £103 / night

(1) Excellent 

22

Holiday home letting

Southwest Gulf Coast / Port Charlotte

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 8 km
  • Suitable for children age 5+

from £67 / night

£400 - £681 / week

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from £67 / night

(22) Very Good 

30

Apartment rental in Florida with golf nearby

Florida / Clearwater

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 5 km
  • Swimming pool
“Very Enjoyable Stay” We had a great stay at Lake Tarpon Villas. The condo was extremely clean when we arrived and was very comfortable. Everything you needed was in the condo and made our stay very enjoyable. The location was perfect for us as it was
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from £55 / night

£300 / week

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from £55 / night

(21) Very Good 

18

Kissimmee holiday villa rental

Central Florida / Kissimmee

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“I would return to this villa anytime” location was great, attractions within easy reach, restaurants and shops within easy reach, very clean villa with plenty of everything, pool was clean and inviting, loved it.
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from £65 / night

£450 - £500 / week

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from £65 / night

1