50 Best Vacation Rentals in North America - Holiday Lettings - Cabins

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158,380 Vacation rentals

(50) 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 $63 / night

$438 - $619 / week

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from $63 / night

(5) Very Good 

38

Vacation bungalow in Davenport

Central Florida / Davenport

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • 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 $63 / night

$500 - $688 / week

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from $63 / night

(5) Excellent 

27

Cottage rental in Huntsville

Muskoka District / Huntsville

4 12 Min stay varies

  • 4 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 14 mi
  • Child friendly
In search of privacy, stunning views, beautiful natural waterfront and outstanding accommodation? This impressive architect owned and designed cottage delivers. Watch heron fly into the wetlands or otter swim by. Relax ... you have found "Serenity".On Otte  …see more

from $591 / night

$5612 - $7708 / week

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from $591 / night

Featured properties

(11) Excellent 

14

Apartment rental in Friars Hill with shared pool, golf nearby

Antigua / Friars Hill

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary
Situated on the beach on Dickenson Bay, one of the Caribbean's most highly rated beaches, our studio apartment is one of just 98 privately owned, and situated on the same beach and next to Sandals grande Antigua.Furnished with a new king size bed and double  …see more

from $125 / night

$875 - $1375 / week

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from $125 / night

33

Vacation cottage in Muskoka Lakes

Muskoka District / Muskoka Lakes

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
Muskoka Silver Pines Cottage is a very private waterfront 4 season cottage with all the comforts of home. It is conveniently located less than 2 hours from the GTA, on beautiful McTaggart Lake. The Muskoka cottage is all set for a Family Fun Retreat or a relaxing  …see more

from $225 / night

$1011 - $2021 / week

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from $225 / night

(28) Very Good 

24

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 $44 / night

$274 - $469 / week

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from $44 / night

(4) Good 

45

Vacation apartment in Miami Beach

Florida / Miami Beach

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
Welcome to Seacoast apartment. Enjoy your vacation on Miami Beach in an extraordinary, newly renovated two bedroom apartment. This unit is a two bedroom, 2 bath master, apartment full of new furniture and is extremely spacious! The master bedroom has one King bed while  …see more

from $175 / night

$1525 / week

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from $175 / night

(23) 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 $122 / night

$788 - $875 / week

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from $122 / 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

$1155 - $1722 / week

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from $155 / night

(11) Excellent 

19

Vacation cottage in Maracas Bay

Trinidad / Maracas Bay

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 9 mi
  • Private garden
La Vapeur Estate is located at the summit at the third highest point in Trinidad, which is located in the southern Caribbean. With stunning sea and mountain views, the property's wood cabin offers a private, luxurious and serene getaway with spectacular views of th  …see more

from $99 / night

$693 / week

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from $99 / night

60

Basse-Terre Island / Sainte Rose

4 16 7 nights min

  • 4 bedrooms
  • Sleeps 16
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning

 …see more

from $154 / night

$1078 - $1741 / week

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from $154 / night

(2) Excellent 

18

Quathiaski Cove Vacation cottage rental

Quadra Island / Quathiaski Cove

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Nearest beach 20 mi
Cabin On The Cove is beautifully situated on Quadra Island, BC, the largest of the Discovery Islands. Visitors come in all seasons, drawn by the breathtaking coastal scenery and many recreational opportunities offered by this small group of islands located along the Ins  …see more

from $113 / night

$738 - $936 / week

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from $113 / night

(19) Excellent 

29

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  …see more

from $81 / night

$563 - $625 / week

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from $81 / night

(12) 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 ho  …see more

from $82 / night

$569 / week

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from $82 / 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 $83 / night

$575 - $625 / week

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from $83 / night

(43) Excellent 

47

Orlando Vacation villa rental

Orlando / Orange Tree

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Nearest beach 127 mi
  • Swimming pool
  • Child friendly
5 bedroom and 4 bathrooms makes Heron Villa an ideal choice for a large family,two families or smaller parties wishing to enjoy the space. Please view our personal website, WWW.FLORIDAVILLABOOKERS.COM where YOU CAN SEE OUR WALK THROUGH VIDEO, PRODUCED IN APRIL 2016.  …see more

from $117 / night

$813 - $932 / week

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from $117 / night

(11) Excellent 

37

Vacation villa with swimming pool in Davenport

Central Florida / Davenport

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 90 mi
  • Swimming pool
  • Child friendly
The Great Orlando Villa is a fully furnished and recently refurbished holiday villa set in the Bridgewater Crosing community. It has a large central kitchen dining and lounge area that splits the two main sleeping areas. The main bedroom has an en suite and a twin bedde  …see more

from $107 / night

$494 - $744 / week

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from $107 / night

(8) Very Good 

24

Villa rental in Kissimmee with golf nearby

Kissimmee / Oak Island Cove

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 80 mi
  • Swimming pool
Positioned on Oak Island Cove next to Formosa Gardens, this is one of the most exclusive vacation sub rental divisions in Central Florida. Every amenity is close at hand for a wonderful vacation. No other location boasts a 5 minute journey to Disney World, Orlando. The  …see more

from $166 / night

$1157 - $1494 / week

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from $166 / night

(5) Very Good 

5

Quebec / Quebec City

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Ask about children
  • Air conditioning

 …see more

from $57 / night

$393 - $682 / week

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from $57 / 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

$630 - $931 / week

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from $90 / night

(26) 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  …see more

from $83 / night

$578 - $630 / week

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from $83 / night

(45) Excellent 

39

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
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, conservation area and Florida's woodlands. The villa with fully automated Jacuzzi and pool  …see more

from $125 / night

$744 - $1157 / week

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from $125 / night

(16) 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 $95 / night

$663 - $850 / week

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from $95 / night

(17) Excellent 

27

Vacation villa in Kissimmee

Kissimmee / Formosa Gardens

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Nearest beach 100 mi
  • Swimming pool
  • Child friendly
Set in a third of an acre with extensively landscaped gardens and mature palm trees, this spacious (4.000 sq. ft.) luxury home has been professionally furnished and decorated to the highest of standards and enjoys many upgraded facilities including tiling throughout the  …see more

from $179 / night

$1250 - $1625 / week

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from $179 / night

(21) Excellent 

24

Vacation townhouse rental

Kissimmee / Encantada Resort

4 8 5 nights min

  • 4 bedrooms
  • Sleeps 8
  • 5 nights min
  • Nearest beach 50 mi
  • Swimming pool
  • Child friendly
THE HOUSE Interior designed 4 bedroomed house, sleeps 8, with (heated) private pool located in the beautiful 5 star Encantada resort. The resort itself is a "Hidden Gem" with the lake-facing property situated just a stone's throw away from the main  …see more

from $125 / night

$850 - $1188 / week

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from $125 / night

(17) Very Good 

18

Kissimmee Vacation villa rental

Central Florida / Kissimmee

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Our villa is furnished to the highest standard and has the WOW factor. The villa has recently been tiled from the Great Room to the Living Room and new carpets in all the bedrooms.From the large hallway it opens up to the large Great room with wall to wall mirrors g  …see more

from $82 / night

$563 - $625 / week

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from $82 / night

(6) Very Good 

24

Vacation cottage with golf nearby in New Seabury

Cape Cod / New Seabury

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.5 mi
  • Child friendly
Lovely open-plan home furnished in comfortable, casual style. Fully-equipped kitchen with counter seating, dining area and sitting area with TV, flow into second step-down sitting area which opens with sliding glass doors onto deck and back yard. Master bedroom (with  …see more

from $145 / night

$995 - $2695 / week

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from $145 / night

(10) 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 an  …see more

from $94 / night

$657 - $919 / week

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from $94 / night

(2) Very Good 

24

Vacation condo with shared pool in Sunny Isles Beach

Florida / Sunny Isles Beach

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.15 mi
  • Swimming pool
Looking for the best place to enjoy Miami Beach?With 'Rent Miami 305' you can enjoy world-class luxury at an affordable price. If you are travelling on your own, with family or friends, our residence has 2 bedrooms (1st bedroom has a king size bed and  …see more

from $130 / night

$910 / week

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from $130 / night

(14) Excellent 

18

Vacation villa in Davenport

Davenport / Tuscan Hills

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Welcome to our stunning, spacious, luxury villa on the prestigious gated resort of Tuscan Hills.Beautifully furnished throughout, the villa comes complete with all the facilities you would expect from a Disney dream holiday, including a full games room, high spe  …see more

from $88 / night

$625 - $788 / week

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from $88 / night

(2) Very Good 

11

Guadeloupe / Saint Anne

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 300 mi
  • Child friendly

 …see more

from $44 / night

$302 - $604 / week

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from $44 / night

(13) 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 $123 / night

$858 - $1007 / week

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from $123 / night

(29) Excellent 

90

Villa rental in Kissimmee with swimming pool

Kissimmee / Eagle Pointe

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Our beautiful villa is located just minutes away from the Disney theme parks and other attractions in Orlando, Florida. For the holiday of a lifetime, a vacation in our villa will provide you with spacious accommodation and your own private, south-facing swimming pool w  …see more

from $82 / night

$569 - $692 / week

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from $82 / night

(28) Excellent 

24

Kissimmee Vacation villa rental

Central Florida / Kissimmee

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • 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 $113 / night

$788 - $1025 / week

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from $113 / night

(4) Excellent 

13

Penthouse accommodation in Speightstown

Saint Peter Parish / Speightstown

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Car not necessary
Located on the edge of charming and historic Speightstown on the West Coast of Barbados is this fully air conditioned 3 bedroom 3 en suite bathroom, 1,700 sq ft beachfront penthouse duplex apartment with high vaulted ceilings covered and uncovered terrace with sea and b  …see more

from $188 / night

$1313 - $2188 / week

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from $188 / night

(27) Very Good 

12

Villa rental in Kissimmee with swimming pool

Kissimmee / Lindfields

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Sunrise Villa is a luxurious villa close to all major attractions in a quiet, private & gated community in the town of Kissimmee. Our rate is from £400 per week .We are only 25 minutes from the airport & a stones throw away from Walt Disney World Orlando.  …see more

from $77 / night

$532 - $750 / week

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from $77 / night

(20) Very Good 

68

Vacation villa in Kissimmee

Kissimmee / Lindfields

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Luxurious Detached Villa- 5 Bedrooms - 3 Baths - (Sleeps 12)Simply the best location! Just a ten-minute drive from the Disney Theme parks but set in the quiet haven of the prestigious Lindfields Estate. This luxury villa sleeps up to 12 people and is beautifully  …see more

from $125 / night

$563 - $675 / week

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from $125 / night

(1) Excellent 

24

Clinton Vacation home rental

Prince Edward Island / Clinton

4 9 7 nights min

  • 4 bedrooms
  • Sleeps 9
  • 7 nights min
  • Child friendly
Island Crest Chalet sits atop the rolling hillside and overlooks the picturesque Southwest River. The open-concept cathedral chalet has a 40' wall of windows and large deck that provides an eagle's eye view of the water for you to enjoy while relaxing on vacat  …see more

from $168 / night

$1176 - $1662 / week

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from $168 / night

23

Grande-Terre Island / Sainte-Anne

3 5 7 nights min

  • 3 bedrooms
  • Sleeps 5
  • 7 nights min
  • Child friendly

 …see more

from $70 / night

$485 - $539 / week

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from $70 / night

(2) Excellent 

18

Condo rental in Lowlands with shared pool, golf nearby

Tobago / Lowlands

2 8 Min stay varies

  • 2 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 1 mi
  • Swimming pool
  • Child friendly
It's a ground floor condo overlooking the Tobago Plantations golf course. tranquil and peaceful surroundings. Access to 3 separate pools on compound and Lowlands beach. Sleeps 8 comfortably. Perfect for small families with young children. Cable television and wifi  …see more

from $180 / night

$1260 / week

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from $180 / night

1