50 Best Florida Vacation rentals on Holiday Lettings - Beach rentals

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36,388 Vacation rentals

Travelers going to Florida are booking December dates now. Secure your vacation rental today and have the perfect trip.

(1) Excellent 

20

Boynton Beach Vacation villa rental

Florida / Boynton Beach

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 5 mi
  • Swimming pool
Magnificent lakeview villa in a very safe and quite gated community in Boynton Beach - Palm Beach County . The property has a very large master with en suite His & hers dressing and bathroom . The bathroom has a two sink vanity , Jacuzzi and separate shower . Two addi  …see more

from $200 / night

$1400 / week

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from $200 / night

(9) Excellent 

17

Vacation apartment in Bradenton

Southwest Gulf Coast / Bradenton

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 12 mi
  • Swimming pool
Our light, spacious, open-plan apartment is in the Shorewalk complex, situated on the beautiful central Gulf Coast of Florida.  Shorewalk comprises 2-story buildings on 30 acre grounds with mature trees.  Paths, well-lit at night, meander around 6 stocked lakes to l  …see more

from $88 / night

$596 - $899 / week

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from $88 / night

(23) Excellent 

24

Vacation condo with golf nearby in Orlando

Orlando / Vista Cay

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • 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 sta  …see more

from $82 / night

$569 - $641 / week

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from $82 / night

(17) 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 $68 / night

$700 - $1042 / week

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from $68 / night

(1) Very Good 

31

Vacation villa in Orlando

Central Florida / Orlando

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
PLEASE NOTE THIS VILLA IS AVAILABLE FOR MINIMUM OF 5NIGHTS Stunning 5 bedroom villa, sleeps 10, in Highlands Reserve Championship Golf Community and the perfect location for visiting Disney World (only a 15minute drive). This spacious 3500 square foot two storey home  …see more

from $143 / night

$996 / week

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from $143 / night

(19) 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 $140 / night

$880 - $1041 / week

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from $140 / night

(12) Very Good 

24

Kissimmee Vacation villa rental

Kissimmee / Cumbrian Lakes

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Premier, 2 storey, south facing villa with wonderful, private, lake & conservation views. BEST LOCATION in CUMBRIAN LAKES with an extra large lanai pool/spa area, 5 bedrooms & 3.5 bathrooms in the fabulous secure gated community of Cumbrian Lakes with free Wi Fi + 55" f  …see more

from $100 / night

$699 - $1016 / week

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from $100 / night

(13) Excellent 

25

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 Ri  …see more

from $140 / night

$981 - $1275 / week

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from $140 / night

(6) Very Good 

20

Vacation villa rental

Kissimmee / Emerald Isle Kissimmee

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Nearest beach 120 mi
  • Swimming pool
  • Child friendly
A luxurious 4 bedroom, 3 bathroom vacation villa features a large private south facing pool and spa with conservation view plus fully air conditioned rooms and tv's and dvd's in living room and all bedrooms. The home is on the superb Emerald Island Resort and close to  …see more

from $96 / night

$667 - $845 / week

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from $96 / night

(25) Very Good 

18

Kissimmee Vacation townhouse rental

Kissimmee / Venetian Bay Villages

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 55 mi
  • Swimming pool
Enjoy the comforts of our 3 bedroom, 2 bathroom town home which will sleep 6. The home was newly built in Jan 2004 and is located on a gated community in Kissimmee (just off the US192) 15 mins from Disney. Wi-Fi internet access provided in the home.On site f  …see more

from $54 / night

$374 - $454 / week

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from $54 / night

(19) Very Good 

17

Clermont Vacation villa rental

Clermont / Greater Groves

5 12 1 night min

  • 5 bedrooms
  • Sleeps 12
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning
Tangerine Villa is a stylish Floridian Home which is luxuriously equipped to the highest standards. This spacious, single-story home of four to five bedrooms with three bathrooms offers accommodation for up to ten people. The villa is fully air conditioned and has its o  …see more

from $89 / night

$521 - $629 / week

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from $89 / night

(11) Excellent 

26

Orlando Vacation villa rental

Central Florida / Orlando

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Amazingly beautiful Privately Owned 5 bed 3 bath home with gorgeous private south west facing 30ft swimming pool and spa with HEATING INCLUDED ALL YEAR ROUND !! A huge covered lanai for lovely outside dining and stunning views over conservation areas. With over 3500sq  …see more

from $191 / night

$1334 - $2223 / week

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from $191 / night

(3) Very Good 

16

Vacation villa in Rotonda West

Southwest Gulf Coast / Rotonda West

4 10 7 nights min

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
A superb 4/5 bedroom home with everything you could wish for in a holiday home. Perfect surroundings, ideal outlook over a lake and golf course, many upgrades are included free of charge, internet, Wi Fi connection, satellite TV, TV's in living and both master sui  …see more

from $127 / night

$756 - $1264 / week

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from $127 / 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 mi
  • Swimming pool
  • Child friendly
Situated within the popular Solana Resort, and close to a local supermarket and restaurants this beautiful 4 bedroom three bathroom villa sleeps up to 8 people and also benefits from an extensive range of resort facilities.Set on a single level, our beautiful an  …see more

from $90 / night

$631 - $932 / week

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from $90 / night

(42) Excellent 

91

Vacation villa in Kissimmee

Kissimmee / Westside

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Nearest beach 96 mi
  • Swimming pool
  • Child friendly
La Bella Vita is our newly refurbished Italian-style villa featuring 4 luxury bedrooms and 3.5 bathrooms in the highly desirable Westside community of Calabria and West Tuscany. A perfect location for your family vacation to Disney. It is situated in Kissimmee and jus  …see more

from $121 / night

$826 - $1175 / week

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from $121 / night

(12) 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 $200 / night

$1394 / week

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from $200 / night

(43) Excellent 

40

Kissimmee Vacation villa rental

Kissimmee / Westside

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
5 night gap in December for just £450 - a saving of £75 from the advertised price. This exclusive luxury property, with beautiful Italian themed fixtures and fittings is set in the highly desirable community of (Tuscany/Calabria) surrounded by small lakes, conservati  …see more

from $115 / night

$756 - $1080 / week

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from $115 / night

(22) 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 wo  …see more

from $90 / night

$631 - $1016 / week

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from $90 / night

(13) Excellent 

24

Davenport Vacation home rental

Davenport / Regal Palms

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
REDUCED REPORT FEE FOR BOOKINGS OF 30 DAYS AND OVER DURING OCTOBER-MARCH We fell in love with Regal Palms as soon as we saw the magnificent lazy river, 2 heated pools, waterslide, jacuzzi, sauna, steamroom and fitness centre. Our son did test out the lazy river, waters  …see more

from $83 / night

$575 / week

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from $83 / night

36

Vacation townhouse with swimming pool in Orlando

Orlando / Encantada

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 80 mi
  • Swimming pool
Private screened pool, full kitchen amenities, microwave, playground area, DVD, fully furnished, self-catering, clubhouse,community pools, washer dryer, gated, arcade, cyber cafe, sundry shop, fishing,wine bar, gym and more, pool tables, wireless Internet, jacuzzi, secl  …see more

from $115 / night

$750 - $1051 / week

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from $115 / night

(5) Excellent 

16

Vacation villa with swimming pool in Kissimmee

Kissimmee / Eagle Pointe

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
When on holiday if you what to retain a bit of independence then a stay in your very own Villa is a perfect way to do it. Our Disney area villa comes with its very own private swimming pool where you can escape all the thrills and spills down the road and have some quie  …see more

from $95 / night

$650 - $1295 / week

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from $95 / night

(11) Excellent 

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

from $83 / night

$578 / week

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from $83 / night

(23) Excellent 

8

Vacation condo in Kissimmee

Kissimmee / Cane Island

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Cane Island is a luxurious gated resort featuring impressive amenities. Our Condo is located on the ground floor, it is a 2 bedroomed condo that is perfectly accessible for both wheelchairs and pushchairs, everything is on a level so there are no steps or ramps.  …see more

from $64 / night

$445 - $534 / week

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from $64 / night

(27) Very Good 

24

Vacation condo with golf nearby in Kissimmee

Central Florida / Kissimmee

3 6 4 nights min

  • 3 bedrooms
  • Sleeps 6
  • 4 nights min
  • 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 - $426 / week

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from $45 / night

(20) 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 $178 / night

$1596 - $1945 / week

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from $178 / night

(21) 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 Fo  …see more

from $96 / night

$667 - $762 / week

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from $96 / night

(22) Excellent 

16

Orlando Vacation villa rental

Orlando / Westridge

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
With a south and west facing pool you are guaranteed the maximum sunshine available here in sunny Florida, but there is also enough shade if you want to cool down a little. Having two sitting areas, Jasmine Villa has enough room for everyone to be able to lounge in comf  …see more

from $110 / night

$762 - $851 / week

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from $110 / night

(30) 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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from $127 / night

(21) 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 $117 / night

$731 - $762 / week

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from $117 / night

(42) Excellent 

21

Vacation villa with golf nearby in Davenport

Central Florida / Davenport

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • 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 minut  …see more

from $64 / night

$445 - $629 / week

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from $64 / night

(7) Very Good 

20

Vacation townhouse in Kissimmee

Kissimmee / Paradise Palms

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Nearest beach 80 mi
  • Swimming pool
  • Child friendly
Paradise Palms is situated in one of the best area's in Kissimmee, only minutes from Disney, Universal Studios, Island of Adventure and sea world. With its terrific shopping malls and fantasic restaurants this is the place to stay.Only a Couple of minutes w  …see more

from $119 / night

$762 - $1194 / week

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from $119 / night

(12) 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 $79 / night

$483 - $635 / week

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from $79 / night

(29) Excellent 

20

Kissimmee Vacation villa accommodation

Central Florida / Kissimmee

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Situated in a quiet, well established residential area our 5 bedroom villa easily accommodates 2 large families. There are 2 large master bedrooms with ensuites, 3 more bedrooms and a further bathroom. Outside space comprises a large private heated swimming pool with c  …see more

from $120 / night

$840 - $920 / week

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from $120 / night

(12) Excellent 

35

Davenport Vacation villa rental

Davenport / Calabay Parc

5 12 4 nights min

  • 5 bedrooms
  • Sleeps 12
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Found on Calabay Parc our private 5-bedroom/4.5-bathroom villa is extremely well equipped to a high standard with all the amenities you would expect for your Florida retreat. It is perfect for 2 families, larger groups or simply those who enjoy plenty of space. Along wi  …see more

from $100 / night

$694 - $1023 / week

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from $100 / night

(14) Excellent 

66

Orlando Vacation villa rental

Central Florida / Orlando

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
***FREE WIRELESS INTERNET JUST BRING YOUR MOBILE DEVICES** ***FREE NATIONAL AND INTERNATIONAL LANDLINE PHONE CALLS*** Sleeps a maximum of 8 adults. As you enter our lovely home, you will be impressed with the soaring 17ft high ceilings in the spacious hallway and li  …see more

from $166 / night

$953 - $1302 / week

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from $166 / night

(10) Excellent 

22

Davenport Vacation villa rental

Davenport / Watersong Resort

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 80 mi
  • Swimming pool
This stunning Orlando Vacation home provides spacious ensuite accommodation for up to 12 guests. Situated on the prestigious Watersong gated community, the villa looks out on beautiful conservation and lake views.The house is furnished to a very high standard an  …see more

from $155 / night

$1156 - $1723 / week

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from $155 / night

(16) 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 $84 / night

$585 - $635 / week

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from $84 / night

(32) Excellent 

23

Davenport Vacation villa rental

Davenport / West Stonebridge

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 141 mi
  • Swimming pool
If you are looking for privacy, space, home from home comforts and your very own pool there is no better alternative than a villa. Our luxury executive villa is situated in a small residential development only a 12 minute drive from Walt Disney World and only a 3 min dr  …see more

from $83 / night

$502 - $667 / week

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from $83 / night

(5) Excellent 

14

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
A really fantastic home for that very special holiday. This home is immaculate throughout. The pool faces southwest, is quite secluded and overlooks a golf course and lake through the trees making this a perfect place to relax and enjoy the Florida sunshine. The pool ha  …see more

from $89 / night

$623 - $1010 / week

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from $89 / night

(11) Very Good 

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 $272 / night

$1901 - $2800 / week

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from $272 / night