50 Best Florida Vacation rentals on Holiday Lettings - Beach rentals

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38,727 Vacation rentals

(3) 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
Beautiful 5 bed villa in Kissimmee, Florida, the holiday destination of the world. Just 10 minutes from Disney in one of the most sought after communities in Orlando. Our villa is luxuriously furnished, with its own secluded pool & spa, a fabulous games room and minutes …see more

from $166 / night

$1156 / week

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from $166 / night

(16) Excellent 

25

Vacation villa with golf nearby in Davenport

Davenport / Sandy Ridge

4 10 Min stay varies

  • 4 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 $125 / night

$1000 - $1200 / week

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avg. 2 hours 53 minutes

from $125 / night

(8) Excellent 

24

Vacation villa in Davenport

Davenport / Highgate Park

4 10 5 nights min

  • 4 bedrooms
  • Sleeps 10
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
The Villa Our luxurious villa is very spacious at 2100 sq ft and comes with all modern amenities. Being set well back from US Hwy 27 it is peaceful and quiet with no noise from passing traffic. The villa is also on a gated community offering further security and …see more

from $100 / night

$699 - $879 / week

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Responds fast!
avg. 2 hours 57 minutes

from $100 / night

(42) Excellent 

31

Vacation 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 mi
  • Swimming pool
AWARDED TRIP ADVISOR CERTIFICATE OF EXCELLENCE 2014!!! Sleeping eight to ten The Little Mermaid Villa gives its guests four bedrooms..two with super king sized beds,with en-suite bathrooms which lead out onto the patio/pool area also large wardrobes with ample …see more

from $121 / night

$845 / week

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from $121 / night

(6) Very Good 

38

Vacation bungalow in Davenport

Central Florida / Davenport

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 70 mi
  • Swimming pool
This fully equipped Executive detached pool villa has 4 bedrooms, 3 baths, open plan great room with dining area kitchen and breakfast nook. The pool and jacuzzi have large deck area with a fan. The property offers two double en suite bedrooms and two twin bedrooms. Gam …see more

from $64 / night

$512 - $705 / week

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from $64 / night

(22) Excellent 

24

Vacation 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
Island setting. 4 Bed, 2.5 Bath Villa, 8 minutes stroll from the lovely Fort Myers Beach.33 Foot Infinity Pool with massage jets giving onto canal (dolphin+manatee visits). Extensive south facing Patio/Deck/Pool area with barbecue.Sleeps up to 8. Beach Equipment + Caddi …see more

from $214 / night

$1495 - $2215 / week

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from $214 / night

(24) 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 f …see more

Certificate of Excellence

from $103 / night

$705 - $832 / week

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Responds fast!
avg. 2 hours 35 minutes

from $103 / night

(1) Very Good 

17

Vacation home in Haines City

Central Florida / Haines City

4 8 5 nights min

  • 4 bedrooms
  • Sleeps 8
  • 5 nights min
  • Child friendly
  • Air conditioning
  • Private garden
Wonderful four bedroom, three bathroom villa centrally located between Walt Disney World Resort and LEGOLAND, FL. This home features two master bedrooms, spa and games room. Fully equipped with everything you will need in a home away from home you couldn't ask …see more

from $145 / night

$1015 / week

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from $145 / night

(11) Very Good 

36

Haines City Vacation villa rental

Haines City / Southern Dunes

4 8 4 nights min

  • 4 bedrooms
  • Sleeps 8
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
4 bedroom, 3 bathroom luxury villa with private pool and games room located on Southern Dunes golf course. Southern Dunes is a gated community located South of Orlando on Highway 27. Community amenities include a large public swimming pool and tennis courts, plus a cham …see more

from $79 / night

$540 / week

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avg. 3 hours 25 minutes

from $79 / night

(5) Excellent 

Certificate of Excellence

13

Orlando Vacation villa rental

Orlando / Westridge

4 8 5 nights min

  • 4 bedrooms
  • Sleeps 8
  • 5 nights min
  • Nearest beach 60 mi
  • Swimming pool
  • Child friendly
Set on a private raised plot in the secluded and peaceful area known as Westridge, this luxurious villa set well back from Highway 27 is just 15 mins from Disney and the theme parks, has close access to supermarkets and golf courses and has a Southwest facing lanai offe …see more

Certificate of Excellence

from $93 / night

$628 / week

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Responds fast!
avg. 2 hours 18 minutes

from $93 / night

(20) 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 $96 / night

$672 / week

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Responds fast!
avg. 2 hours 55 minutes

from $96 / night

(4) Excellent 

34

Davenport Vacation condo rental

Davenport / Bahama Bay Resort

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
The Bahama Bay Resort is Orlando's new, exclusive, secluded and tranquil Caribbean-style Condo resort sitting right on the banks of the picturesque Lake Davenport. The Resort is laid out over 70-acre spread of gardens, lawns, lagoons and fountains, making it a truly …see more

from $58 / night

$401 - $623 / week

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from $58 / night

(57) 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 $134 / night

$934 - $1150 / week

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avg. 1 hour 47 minutes

from $134 / night

(16) Excellent 

30

Clermont Vacation villa rental

Clermont / Greater Groves

4 10 4 nights min

  • 4 bedrooms
  • Sleeps 10
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
4 bedroomed, 2 king, 2 twin (1 Disney themed). Extra large bathroom/bath tub in ensuite. Family lounge area with large leather corner sofa seats 8-10 . Patio furniture for 10 on extra large lanai. Fans outside on lanai. Fans in all major rooms/bedrooms as well as full a …see more

from $103 / night

$705 - $884 / week

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Responds fast!
avg. 1 hour 48 minutes

from $103 / 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 mi
  • Swimming pool
SEE OUR UPDATED IMPRESSIVE GUEST BOOK REVIEWS !! RELAX- The home is fully air-conditioned throughout with sliding patio doors to the private pool area from the lounge and master bedroom too! With a well-appointed dining room, living room, large family room, g …see more

from $85 / night

$700 - $900 / week

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Responds fast!
avg. 3 hours 28 minutes

from $85 / night

(6) Excellent 

24

Haines City Vacation villa rental

Haines City / Calabay Parc at Tower Lake

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Magic Villa Orlando is situated on the secure gated community of Calabay Parc at Tower Lake. The Villa has four bedrooms (2 king size beds, 1 double sized bed, and 1 twin bedroom), all with en suite bathrooms. The villa has a large, modern open plan living and dining …see more

from $109 / night

$762 - $1016 / week

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Responds fast!
avg. 3 hours 20 minutes

from $109 / night

(34) Excellent 

23

Vacation home with swimming pool in Kissimmee

Kissimmee / Oak Island Cove

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Sun Quest Villa is located on the small and peaceful community of Oak Island Cove. The property is an exceptionally spacious and luxuriously decorated 5 bedroom 4 bathroom home with fully screened private pool and hot tub. Oak Island Cove is one of the closest and most …see more

from $127 / night

$762 - $889 / week

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Responds fast!
avg. 1 hour 52 minutes

from $127 / night

(29) 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 $120 / night

$805 - $1120 / week

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Responds fast!
avg. 2 hours 25 minutes

from $120 / night

(10) Excellent 

23

Davenport Vacation villa rental

Davenport / Highgate Park

4 8 6 nights min

  • 4 bedrooms
  • Sleeps 8
  • 6 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This superb home has 4 bedrooms (1 master with king-sized bed, 1 queen-sized bedroom and 2 twin rooms each with 2 single beds). We can therefore accommodate up to 8 people in complete luxury and comfort. There is a large 30ft x 12ft swimming pool with spa, extended pool …see more

from $108 / night

$889 / week

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Responds fast!
avg. 1 hour 2 minutes

from $108 / night

(15) 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 $140 / night

$883 - $1048 / week

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from $140 / night

(18) 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 $100 / night

$699 - $864 / week

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avg. 2 hours 40 minutes

from $100 / night

(3) Excellent 

24

Vacation home rental

Central Florida / Reunion

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
This is an outstanding home which we recently completely renovated, decorated and furnished to the Reunion standard with an updated feel and now presents as an amazing vacation property. The ground floor is very bright and spacious and offers a king-size suit to the f …see more

from $386 / night

$2670 - $3732 / week

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from $386 / night

(18) Excellent 

46

Florida Vacation condo rental

Florida / Indian Rocks Beach

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
A luxurious vacation condo - only steps to the beach and Gulf of Mexico! The wide, sandy beach is just a step down from the pool area and is perfect for sunbathing, shelling, or walking for miles in either direction. This is a small development of 7 condos, our unit …see more

from $135 / night

$950 / week

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from $135 / 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 $90 / night

$506 / week

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from $90 / night

(34) 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 $128 / night

$832 / week

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Responds fast!
avg. 3 hours 17 minutes

from $128 / night

(22) Very Good 

Certificate of Excellence

28

Vacation villa with golf nearby in Rotonda West

Southwest Gulf Coast / Rotonda West

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
An exceptional privately owned villa that has been furnished to a very high standard.It has many upgrades and extras including 3 large bedrooms,master bathroom suite, plus 1 further bathroom.Beautifully decorated with cathedral ceilings plus fully upgraded, well equippe …see more

Certificate of Excellence

from $109 / night

$705 - $1152 / week

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Responds fast!
avg. 3 hours 35 minutes

from $109 / night

(13) Excellent 

Certificate of Excellence

50

Vacation villa rental

Central Florida / Orlando

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 125 mi
  • Swimming pool
  • Child friendly
Our home is a detached four bedroom villa with private pool and Jacuzzi , situated in Weston Hills a quiet residential gated community set in natural surroundings. Weston Hills is located within easy reach of all Orlando's top attractions, ideally situated for a holiday …see more

Certificate of Excellence

from $103 / night

$717 / week

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Responds fast!
avg. 2 hours 3 minutes

from $103 / night

(2) Excellent 

34

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
Villa Betty Boo is on the prestigious Hampton Lakes Community which has a swimming pool, basketball, volleyball and tennis courts for your free use. Hampton Lakes is beautifully landscaped and is a very secure community. Villa Betty Boo has 4 spacious bedrooms and can s …see more

from $100 / night

$700 - $870 / week

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from $100 / night

(2) Excellent 

69

Vacation home in Davenport

Central Florida / Davenport

12 28 Min stay varies

  • 12 bedrooms
  • Sleeps 28
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Why rent hotel rooms?! When you can get a private Disney Golf & Tennis Resort Villa Estate with “the best location” only about 10 minutes from Disney World's Animal Kingdom! 14 Room Disney Area Golf Resort Villa with FREE Tennis, Discount Golf & SPA (Disney Estat …see more

from $397 / night

$1970 - $4970 / week

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from $397 / night

(24) 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 $109 / night

$705 - $768 / week

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from $109 / night

(27) Excellent 

24

Vacation condo with golf nearby in Orlando

Orlando / Vista Cay

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 90 mi
  • Swimming pool
  • Child friendly
The Isles at Cay Commons will entice you with its Tuscan themed condominiums conveniently located less than a mile from International Drive and the Orlando Convention Centre, with the I4 less than 5 minutes drive. You are truly in the “Heart of Orlando” when you stay at …see more

from $85 / night

$592 - $646 / week

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Responds fast!
avg. 2 hours 43 minutes

from $85 / night

(17) Excellent 

22

Vacation villa with golf nearby in Rotonda West

Rotonda West / Broadmoor

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 4 mi
  • Swimming pool
This privately own Villa is rented directly from its U.K. owners with no agents or commissions. It is maintained in lovely condition by the owners and their local professional management company who are always available should you need help or advice. This …see more

from $92 / night

$640 - $672 / week

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Responds fast!
avg. 1 hour 35 minutes

from $92 / night

(9) Excellent 

14

Spring Hill Vacation home rental

Florida / Spring Hill

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Situated in Florida's Gulf Coast, Spring Hill is a 10-15 drive to beautiful beaches, numerous golf courses, wildlife parks, restaurants and of course shops. An excellent base for exploring the metropolis of Tampa, St.Petersburg and Clearwater without the hussle and …see more

from $123 / night

$860 / week

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avg. 3 hours 32 minutes

from $123 / night

(3) Excellent 

23

Old Town Vacation townhouse rental

Florida / Old Town

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
4 Bedrooms / 3 bathrooms - ground floor comprising covered entrance porch, entrance foyer, kitchen, dining area, great room, covered terrace, ground floor double bedroom with bathroom. Stairs leading to - First floor comprising master bedroom with walk in wardrobes and …see more

from $77 / night

$538 - $807 / week

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avg. 2 hours 44 minutes

from $77 / night

(31) Very Good 

23

Vacation condo with golf nearby in Kissimmee

Central Florida / Kissimmee

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 106 mi
  • Swimming pool
  • Child friendly
A perfect location for all that central Florida has to offer, for Mickey fans, serious shoppers, sun worshippers, delicious dining, space shuttle launches, big thrills and spills, airboat adventures, palm trees and pina-coladas! All in the fantastic Sunshine State! Win …see more

from $45 / night

$279 - $477 / week

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Responds fast!
avg. 3 hours 29 minutes

from $45 / night

(13) Excellent 

26

Vacation villa in Orlando

Central Florida / Orlando

6 13 Min stay varies

  • 6 bedrooms
  • Sleeps 13
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
By now, you have looked at 100s of villas in the Disney area. So why this one? Well, it is new, 15 mins from Disney World, luxuriously furnished, with seven HD TVs all with DVR, two entertainment areas, a private pool with jacuzzi, a games room with pool table, darts an …see more

from $149 / night

$1043 - $1758 / week

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from $149 / night

(5) Excellent 

32

Vacation home rental

Southwest Gulf Coast / Cape Coral

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 16 mi
  • Swimming pool
This large open concept home offers 2100 square feet of luxury living. The home itself which features beautiful Turkish marble floors throughout offers 3 large bedrooms and two luxury bathrooms. The home's kitchen features high quality Cherry wood cabinetry, a one of …see more

from $129 / night

$900 - $1350 / week

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Responds fast!
avg. 3 hours 2 minutes

from $129 / night

(2) Excellent 

10

Vacation villa rental

Rotonda West / Long Meadow

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 7 mi
  • Swimming pool
WOW, this really is one of the loveliest homes on the whole of Rotonda, in fact, in my humble opinion probably most of Florida! Fantastic outlook to the rear overlooking the lovely lake and golf course, private yet not secluded. Stunning inside and exceptionally …see more

from $108 / night

$756 - $1461 / week

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Responds fast!
avg. 3 hours 41 minutes

from $108 / night

(5) Excellent 

28

Vacation condo in Florida

Florida / Anna Maria Island

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Located in the heart of Anna Maria Island in the sun-drenched community of Holmes Beach is 'Seacrest' where you can enjoy island living at its best in this stunning destination.Our light & roomy 2 bedroom condo (one of only four in a quiet location being in a little cul …see more

from $102 / night

$711 - $1767 / week

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Responds fast!
avg. 3 hours 54 minutes

from $102 / night

(41) Very Good 

37

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
Affordable comfortable home just ten minutes from Disney. Ideally situated in phase 1 of the resort our home is just a hop skip and a jump away from the fantastic water complex ,clubhouse and restaurant and is extremely popular with repeat guests , some who have …see more

from $90 / night

$700 - $980 / week

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from $90 / night

1