50 Best Florida Vacation rentals on Holiday Lettings - Beach rentals

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36,980 Vacation rentals

(33) Excellent 

24

Kissimmee Vacation villa rental

Central Florida / Kissimmee

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 100 mi
  • Swimming pool
  • Child friendly
Welcome to our 4 bed single storey air conditioned home in Rolling Hills, Kissimee. It is just 10 mins (real time) to Disney Main Gate. It is situated on a part residential, part visitors estate, with lake views at the rear, in a quiet neighbourhood, close to Formosa Ga …see more

from $105 / night

$770 - $910 / week

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Responds fast!
avg. 1 hour 24 minutes

from $105 / night

(25) Excellent 

16

Vacation home rental

Lake County / Clermont

2 4 4 nights min

  • 2 bedrooms
  • Sleeps 4
  • 4 nights min
  • Nearest beach 92 mi
  • Swimming pool
  • Child friendly
Small, detached "House 99" on one floor, Mediterranean roofing. Located between Clermont and Groveland, quiet, sunny position in the countryside, by the lake, by the canal. Great view from the house on the lake, on the garden with its palm trees, oaks and relaxing view …see more

from $150 / night

$950 - $1,040 / week

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avg. 1 hour 22 minutes

from $150 / night

(16) Excellent 

18

Kissimmee Vacation villa rental

Kissimmee / Cumbrian Lakes

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Our villa is south west facing, so when you have had a busy day at the theme parks you can relax with a bbq around the pool, with its covered lania & ceiling fan to watch the sun go down. We have a fully fitted Games room,with pool table, foosball, dart board,Xbox, Wi …see more

from $126 / night

$693 / week

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from $126 / night

(21) Excellent 

12

Vacation villa with golf nearby in Davenport

Davenport / The Manors North at Westridge

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 60 mi
  • Swimming pool
Our one story villa has 4 bedrooms and 3 bathrooms is furnished to a very high standard and comes complete with a large covered sun deck and private outdoor swimming pool.It is situated in an exclusive community accessed by a coded security gate ensuring your privacy an …see more

from $91 / night

$637 - $882 / week

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from $91 / night

(18) Very Good 

42

Palm Harbor Vacation apartment rental

Florida / Palm Harbor

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 5 mi
  • Swimming pool
Ideally located on Florida's Gulf Coast just minutes from many of America’s best beaches. The apartments are situated on the shores of beautiful Lake Tarpon, just north of Clearwater. The big and exciting city of Tampa together with its International Airport is just 30 …see more

from $98 / night

$553 / week

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from $98 / night

(19) Excellent 

34

Orlando Vacation villa rental

Central Florida / Orlando

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Welcome to Ashland Palms – A truly luxurious and spacious executive 4 Bedroom, 3 Bathroom villa in an ideal location to enjoy the many superb Orlando attractions as well as a tranquil haven where you can relax in the south facing pool & spa in the glorious Florida Sun. …see more

from $147 / night

$973 - $1,155 / week

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from $147 / night

(67) Excellent 

77

Vacation villa in Orlando

Orlando / Orange Tree

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
''Sunny Days" Villa is the perfect place to wake each day. Open the doors from your master bedroom, step out on to the pool deck and breathe in the fresh scent of orange blossom.This four bedroom, three bathroom, luxury villa which sleeps eight people is very much a ho …see more

from $152 / night

$1,050 - $1,323 / week

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avg. 2 hours 33 minutes

from $152 / night

(15) Excellent 

25

Vacation home accommodation

Fort Myers Beach / Estero Island

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.3 mi
  • Swimming pool
Bay Front Dream Home. If the water is your passion, come stay in this beautiful bayfront home. Bring your morning cup of coffee to the screen-enclosed pool and lanai to watch the sunrise over Estero Bay. Enjoy fishing from the boat dock, watch the dolphins or its just …see more

from $291 / night

$2,033 - $3,409 / week

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from $291 / night

(15) Very Good 

30

Vacation 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 mi
  • Swimming pool
Our newly remodeled Villa has about 2,000 sq.ft. Living area with 1,100 sq.ft. Generous pool area. You will be love the heated pool with the separate Scandinavian style SPA (Jacuzzi). Within only 3 minutes by boat you’ll reach the high-speed areas on Caloosahatchee Rive …see more

from $140 / night

$980 - $1,275 / week

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from $140 / night

(24) Excellent 

Certificate of Excellence

12

Kissimmee Vacation villa rental

Central Florida / Kissimmee

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Our luxury villa is situated in Country Creek Estates, just off Highway 192 in Kissimmee. The villa offers a high standard family accommodation and all that you need for a relaxing stay with us in Florida.This air conditioned villa comprising 1650 square ft, is locate …see more

Certificate of Excellence

from $128 / night

$770 - $1,050 / week

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avg. 1 hour 33 minutes

from $128 / night

(10) Excellent 

24

Kissimmee Vacation villa rental

Kissimmee / Doral Woods

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
The exclusive woodland setting of Doral Woods is an excellent place for relaxation and yet is within convenient reach of all the action of Disney, Universal, Sea World and Legoland and the other attractions. Be at one with nature in our unspoilt landscape. You can enjoy …see more

from $114 / night

$798 - $1,302 / week

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from $114 / night

(88) Excellent 

Certificate of Excellence

22

Vacation villa in Kissimmee

Kissimmee / Bass Lakes Estate

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 80 mi
  • Swimming pool
RATED EXCELLENT on Trip Advisor with 85 reviews Orlando Florida is the perfect holiday destination for all ages with sunshine all year round. It hosts the world's greatest theme parks and most, including Disney World, are very conveniently located to our villa within 15 …see more

Certificate of Excellence

from $98 / night

$679 - $840 / week

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Responds fast!
avg. 1 hour 55 minutes

from $98 / night

(15) Excellent 

30

Kissimmee Vacation villa rental

Kissimmee / Windsor Palms

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Windsor Palms is a fabulous resort style community and has all the facilities that you would expect from its 5 star status all completely free when you stay at Disney Paradise. It is one of the closest communities to Disney located along Formosa Gardens Boulevard just …see more

from $135 / night

$910 - $980 / week

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Responds fast!
avg. 3 hours 12 minutes

from $135 / night

21

Vacation villa with golf nearby in Davenport

Central Florida / Davenport

4 8 4 nights min

  • 4 bedrooms
  • Sleeps 8
  • 4 nights min
  • Nearest beach 100 mi
  • Swimming pool
  • Child friendly
Our villa 'Savannah' is a really lovely 4 bedroom 3 bathroom fully air-conditioned villa with its own South Facing screened pool and patio area, a beautiful home from home on the Secure & prestigious Highgate Park gated community. Close to Disney (10 minutes), Universal …see more

from $89 / night

$616 - $765 / week

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from $89 / night

9

Apartment accommodation in Sanibel Island

Southwest Gulf Coast / Sanibel Island

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
This excellent Timeshare waterfront resort is set on a west coast island that is world-renowned for its shelling beaches. This ground floor condo is located in Lighthouse Resort and Club --a luxury waterfront resort on the world top rated Sanibel Island, Florida . The s …see more

from $210 / night

$1,050 / week

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from $210 / night

(29) Excellent 

Certificate of Excellence

26

Vacation villa in Davenport

Davenport / Westhaven

5 12 7 nights min

  • 5 bedrooms
  • Sleeps 12
  • 7 nights min
  • Nearest beach 90 mi
  • Swimming pool
  • Child friendly
Cead Mile Failte- a hundred thousand welcomes. The Hamlet at West Haven says Quality, from the minute you leave Ronald Reagan Parkway and enter the first of two tree-lined avenues.Whether you have spent the day at one of the many theme parks or ventured further to Kenne …see more

Certificate of Excellence

from $150 / night

$1,050 - $1,190 / week

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from $150 / night

(14) 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 mi
  • Swimming pool
This beautiful, three bedroom home is both spacious and well-designed. Built in 2003, it provides all the modern amenities you would expect in a family home. It also has a large heated private pool and spa with screened lanai overlooking a tranquil lake. Both pool and l …see more

from $179 / night

$1,250 - $1,850 / week

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from $179 / night

(30) Very Good 

Certificate of Excellence

24

Vacation villa in Orlando

Central Florida / Orlando

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Nearest beach 70 mi
  • Swimming pool
  • Child friendly
Beautiful and luxuriously furnished 4 bedroom villa in the prestigious Glenbrook Resort located within 15 minutes of Walt Disney World. The extra large (30'x15') screened pool and deck are not overlooked, facing onto open conservation lands. The pool deck benefits from …see more

Certificate of Excellence

from $112 / night

$770 - $1,050 / week

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Responds fast!
avg. 2 hours 12 minutes

from $112 / night

(31) Excellent 

53

Orlando Vacation villa rental

Central Florida / Orlando

5 8 Min stay varies

  • 5 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Be Our Guest at Jenny's luxury villa, in the sort after area of Sandy Ridge near Championsgate just off the Interstate 4 (I4). Very easy to get any where. It's in a secluded position overlooking beautiful conservation land. With a 30' x 15' south facing pool and spa, …see more

from $152 / night

$1,043 - $1,246 / week

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from $152 / night

(24) Excellent 

31

Davenport Vacation villa rental

Davenport / Marbella Resort

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Nearest beach 100 mi
  • Swimming pool
  • Child friendly
Situated in a gated community in a peaceful location in Davenport, the Villa benefits from its own private pool & jacuzzi, the pool has shallow end perfect for the children. The villa consists of one twin, one double and two master queen suites, both with en-suites idea …see more

from $95 / night

$665 - $735 / week

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Responds fast!
avg. 2 hours 20 minutes

from $95 / night

(35) Very Good 

56

Vacation villa with shared pool in Orlando

Orlando / Sunrise Lakes

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Nearest beach 90 mi
  • Swimming pool
  • Child friendly
Our luxury Florida vacation rental villa has been designed and furnished to the highest standard to give guests the luxurious holiday they deserve. It has a 28' heated pool with a lake view. We provide free phone calls (US/Canada) so you can tell everyone what a wonderf …see more

from $135 / night

$910 - $1,225 / week

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Responds fast!
avg. 1 hour 36 minutes

from $135 / night

(11) Very Good 

Certificate of Excellence

24

Villa rental in Kissimmee

Central Florida / Kissimmee

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
THE VILLA with it,s fully screened, south facing 30x15ft swimming pool with underwater lighting for evening swimming and has free solar heating with electronic control and electric heating for the winter months. The large deck with sun or shade is equipped with new luxu …see more

Certificate of Excellence

from $105 / night

$735 / week

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Responds fast!
avg. 22 minutes

from $105 / night

(25) Very Good 

23

Vacation villa in Kissimmee

Kissimmee / Kissimmee City

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 60 mi
  • Swimming pool
  • Child friendly
A 3 bedroomed villa which sleeps 6. Approximately 3 miles Disney. Own screened swimming pool with large decking area with gas barbecue with patio furniture and loungers. The villa inside is decorated with blinds and window pelmets. 3 TV's all with cable, VCR and a Mu …see more

from $70 / night

$490 - $693 / week

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from $70 / night

(26) Very Good 

58

Vacation villa in Davenport

Davenport / Sandy Ridge

5 10 1 night min

  • 5 bedrooms
  • Sleeps 10
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning
Our outstandingly beautiful 5 bedroom, 3 bathroom villa is ideally located being just 10 minutes away from all the Disney Theme Parks in Florida on a very sought after estate close to the Champions Gate golfing complex on I4, J58. Our villa has been furnished and is ma …see more

from $130 / night

$910 / week

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Responds fast!
avg. 1 hour 50 minutes

from $130 / night

(3) Excellent 

16

Vacation villa in Kissimmee

Kissimmee / Indian Creek

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Nearest beach 90 mi
  • Swimming pool
  • Child friendly
This superior Executive 4 bedroom villa is only a few short miles from Magic Kingdom,Epcot,Universal Studios (Harry Potter World) and all major attractions. Many homes promise luxury executive accommodation, but just compare with our home before you choose. Our 4 bedroo …see more

from $115 / night

$805 - $1,155 / week

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Responds fast!
avg. 1 hour 57 minutes

from $115 / night

(3) Excellent 

24

Davenport Vacation villa rental

Davenport / West Haven

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
2015 - NEWLY INSTALLED GAMES ROOM COMPLETE WITH POOL TABLE This executive four bedroom, three bathroom Florida villa is located within the prestigious gated community of The Sanctuary at West Haven. Ideally placed for easy access you can reach all the main attra …see more

from $112 / night

$735 / week

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Responds fast!
avg. 2 hours 45 minutes

from $112 / night

(19) Excellent 

25

Vacation villa with golf nearby in Davenport

Davenport / Sandy Ridge

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Nearest beach 90 mi
  • Swimming pool
  • Child friendly
DISNEY Vacation Villa 5 Bedroom 15 Mins to DISNEY, FREE WiFi This very bright and airey home has everything you want from a Florida Disney vacation villa, just turn up with your suitcases and your vacation/holiday starts here. The living room and formal dining area al …see more

from $115 / night

$840 - $1,200 / week

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Responds fast!
avg. 1 hour 59 minutes

from $115 / night

(1) Excellent 

25

Villa rental in Orlando

Central Florida / Orlando

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Beautifully furnished executive home on gated community near Disney. Welcome to our beautiful Orlando villa set in a gated community within a quiet Cul-de-Sac. 10 minutes from Disney with Championsgate golf, shopping and restaurants nearby. Just up the 27 is a Walmart f …see more

from $117 / night

$812 - $1,372 / week

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from $117 / night

(8) Excellent 

Certificate of Excellence

48

Clermont Vacation villa rental

Clermont / Clear Creek

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 100 mi
  • Swimming pool
  • Child friendly
Waterside villa for rent in Orlando (Clermont) Florida. Beautiful villa with king and queen master suites, two twin bedrooms and three bathrooms. The fully screened pool deck is in a position that gets continuous sunshine and is complete with sun loungers and a barbecue …see more

Certificate of Excellence

from $100 / night

$700 / week

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Responds fast!
avg. 2 hours 9 minutes

from $100 / night

(21) Very Good 

Certificate of Excellence

70

Orlando Vacation villa rental

Orlando / The Retreat Legacy Park

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Sunseekersvilla is nestled just minutes away from championship golf courses and the fun-in-the-sun of Disney at Legacy Park, and will leave you with memories to treasure for a lifetime. Located near to Mickey and his friends, this 5 bedroom and 4.5 bathroom elegant Orla …see more

Certificate of Excellence

from $152 / night

$990 - $1,235 / week

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Responds fast!
avg. 54 minutes

from $152 / night

(41) Excellent 

63

Villa rental in Orlando

Orlando / Westridge

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Our villa is in Davenport, about 20 minutes drive from the major theme parks – Disney, Universal, Sea World, etc – and backs on to the beautiful Florida nature reserve. The villa is modern and beautifully furnished, providing a spacious and luxurious base for your Flori …see more

from $140 / night

$910 / week

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Responds fast!
avg. 3 hours 1 minutes

from $140 / night

35

Vacation apartment rental

Florida / Coral Gables

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Bedroom 02 02 01 Full Baths and Toilet, Ritz Carlton Apartment for rent weekly or monthly, located right on Coconut Grove. Fully furnished for up to 6 people. It includes: Free parking, internet, cable, swimming pool, gym and much more! Department 02 bedrooms, 02 bathro …see more

from $150 / night

$1,000 / week

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from $150 / night

(17) Excellent 

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 mi
  • Swimming pool
2200 square feet fully air conditioned living space. Further 800 square feet non air conditioned garage and covered lanai. Beautiful private rear views onto Federal Preserve area. Full electric heated swimming pool with hot tub. Purchased for owners own use as a second …see more

from $110 / night

$770 - $1,106 / week

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from $110 / night

(25) Excellent 

28

Condo rental in Florida

Florida / St. Petersburg

2 6 4 nights min

  • 2 bedrooms
  • Sleeps 6
  • 4 nights min
  • Beach/lakeside relaxation
  • Nearest beach 12 mi
  • Swimming pool
Luxury waterside condo apartment on Florida's Gulf Coast (St. Petersburg) sleeps up to 6 Beautiful apartment in tranquil setting, right on the waterfront with spectacular, open water views over the Big Bayou. Watch the dolphins swim past your private terrace while the …see more

from $119 / night

$770 - $840 / week

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Responds fast!
avg. 3 hours 43 minutes

from $119 / night

(13) Excellent 

Certificate of Excellence

26

Vacation home with golf nearby in Fort Myers

Fort Myers / South Fort Myers

4 10 7 nights min

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 6 mi
  • Swimming pool
Fort Myers is situated in the south west of Florida on the beautiful Gulf Coast, renowned for its long stretches of white sand and the warm waters of the Gulf Stream.Our modern two-storey house (2700 sq feet) is only 3 miles from Fort Myers Beach and 4 miles from the be …see more

Certificate of Excellence

from $133 / night

$973 - $1,119 / week

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Responds fast!
avg. 2 hours 35 minutes

from $133 / night

(7) Excellent 

23

Kissimmee Vacation villa rental

Kissimmee / Country Creek

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Our beautiful family owned villa is located only 10 mins from WDW and close to many other attractions such as Sea World, Aquatica, Universal Studios and Universal Islands of Adventure. Our home from home is comfortably furnished and equipped with all the amenities to m …see more

from $112 / night

$735 - $910 / week

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from $112 / night

(21) Excellent 

22

Vacation villa with golf nearby in Haines City

Haines City / Southern Dunes

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Nearest beach 60 mi
  • Swimming pool
  • Child friendly
Our Villa is located in the beautiful gated community of Southern Dunes overlooking the 3rd green of one of Florida's top rated Golf course's. It has a king-size Master Bedroom with En-suite & 2 Twin Bedrooms with separate bathroom upstairs. Queen Bedroom - with p …see more

from $108 / night

$756 - $805 / week

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Responds fast!
avg. 2 hours 7 minutes

from $108 / night

(31) Very Good 

Certificate of Excellence

36

Vacation villa with swimming pool in Kissimmee

Central Florida / Kissimmee

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Indian Point with gorgeous lake and conservation view from pool. Indian Point, Kissimmee is a beautiful residential community situated within a few minutes drive of the Highway 192, convenient for the Wal-Mart superstore, a large selection of restaurants, and close t …see more

Certificate of Excellence

from $105 / night

$700 - $840 / week

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from $105 / night

(23) Excellent 

15

Orlando Vacation villa rental

Central Florida / Orlando

5 12 7 nights min

  • 5 bedrooms
  • Sleeps 12
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Our 5 bedroom, 3-bathroom villa was built in July 2004 and is located in the Silver Creek Community. Quietly situated in a new tranquil development off Highway 27 just 1-mile from the interchange at Highway 192, the villa is ideally situated for the areas many theme par …see more

from $110 / night

$770 - $994 / week

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Responds fast!
avg. 3 hours 16 minutes

from $110 / night

(15) Very Good 

Certificate of Excellence

90

Vacation townhouse in Kissimmee

Kissimmee / Terra Verde Resort

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 90 mi
  • Swimming pool
  • Child friendly
Palm Heaven Villa has everything you need for a fantastic, relaxing family holiday. Four large bedrooms mean everyone can have plenty of space, and can sleep 8 very comfortably: one queen bedroom is downstairs with an adjacent full bathroom; upstairs is the large master …see more

Certificate of Excellence

from $98 / night

$840 - $1,050 / week

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from $98 / night