Little Harbour Rentals

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1,076 Houses

(2) Very Good 

11

Anani - Kamique

Anguilla / Little Harbour

Little Harbour villa

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Ask about children
  • Ask about pets
“Our Stay at Anani - Kamique” The Villa was fantastic. It overlooks the ocean directly into St Maarten. The accomodations were top quality - TV, appliances, furnishings, etc.
…see more

Price per night from

$1,755

Responds fast!
avg. 1 hour 2 minutes

Price per night from

$1,755

42

Lockrum Point Villa:Ocean front 3-bed/ 3-bath/pool

Anguilla / Little Harbour

Little Harbour villa

3 6 4 nights min

  • 3 bedrooms
  • sleeps 6
  • 4 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$516

Price per night from

$516

32

Ocassa Villa

Anguilla / Little Harbour

Little Harbour villa

5 10 5 nights min

  • 5 bedrooms
  • sleeps 10
  • 5 nights min
  • Ask about children
  • Ask about pets

Price per night from

$1,145

Price per night from

$1,145

16

Anguilla Shores

Anguilla / Little Harbour

Little Harbour villa

2 4 1 night min

  • 2 bedrooms
  • sleeps 4
  • 1 night min
  • Child Friendly

Price per night from

$516

Price per night from

$516

(1) Average 

35

Blue

Anguilla / Little Harbour

Little Harbour villa

10 19 min stay varies

  • 10 bedrooms
  • sleeps 19
  • min stay varies
  • Ask about children
  • Ask about pets

Price per night from

$8,600

Responds fast!
avg. 1 hour 2 minutes

Price per night from

$8,600

(13) Excellent 

29

Three Dolphins Lockrum Bay, Anguilla BWI

Anguilla / Little Harbour

Little Harbour villa

5 10 7 nights min

  • 5 bedrooms
  • sleeps 10
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 1 mi
  • Swimming pool
“Wife's Birthday getaway” After extensive research into renting a property in the islands we found Three Dolphins. Since the trip was for my wife and myself as well as two other couples, the villa was the perfect size. The quality of the villa, the loc
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Price per night from

$2,125

Price per night from

$2,125

39

Lockrum Point Villa

Anguilla / Little Harbour

Little Harbour villa

4 8 4 nights min

  • 4 bedrooms
  • sleeps 8
  • 4 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$575

Price per night from

$575

32

A Spectacular Luxury Villa

Anguilla / Little Harbour

Little Harbour villa

10 20 min stay varies

  • 10 bedrooms
  • sleeps 20
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$9,423

Responds fast!
avg. 4 minutes

Price per night from

$9,423

37

AVALON BEACHFRONT VILLA

Anguilla / Little Harbour

Little Harbour villa

4 10 2 nights min

  • 4 bedrooms
  • sleeps 10
  • 2 nights min
  • Beach / lakeside relaxation
  • Suitable for children age 5+
  • Air conditioning

Price per night from

$1,374

Responds fast!
avg. 1 hour 49 minutes

Price per night from

$1,374

Great rentals within 20 miles that match your search

Distance approx 7.84 km from Little Harbour Show on Map

29

Villa Santai , in a tropical garden ...

Saint-Martin / Orient Bay

Orient Bay villa

2 4 4 nights min

  • 2 bedrooms
  • sleeps 4
  • 4 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$379

Price per night from

$379

Distance approx 6.77 km from Little Harbour Show on Map

(48) Excellent 

52

studio pinel

Saint-Martin / Cul de Sac

Cul de Sac apartment

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning

Price per night from

$138

Responds fast!
avg. 3 hours 30 minutes

Price per night from

$138

Distance approx 11.03 km from Little Harbour Show on Map

(1) Excellent 

15

BEACHFRONTBLISS

Sint Maarten / Simpson Bay

Simpson Bay apartment

2 4 3 nights min

  • 2 bedrooms
  • sleeps 4
  • 3 nights min
  • Beach / lakeside relaxation
  • Ask about children
  • Ask about pets

Price per night from

$345

Price per night from

$345

Distance approx 2.91 km from Little Harbour Show on Map

(13) Excellent 

10

Ocean Terrace Luxury 2BR Condos, Spectacular Views

Anguilla

Anguilla apartment

2 5 2 nights min

  • 2 bedrooms
  • sleeps 5
  • 2 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly
“Love our Vacations at Ocean Terrace” We recently returned from another great stay at Ocean Terrace. We have been visiting for a week each winter since 2009 and love the feeling of returning to our familiar "home" in Anguilla each year. We love the s
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Price per night from

$402

Price per night from

$402

Distance approx 10.35 km from Little Harbour Show on Map

(4) Excellent 

28

Dawn Beach Westin, Very spacious, many services

Sint Maarten / Oyster Pond

Oyster Pond apartment

3 8 7 nights min

  • 3 bedrooms
  • sleeps 8
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$632

Price per night from

$632

Distance approx 1.44 km from Little Harbour Show on Map

(6) Excellent 

19

Imperial Penthouse, New Oceanview w/H.Pool&Package

Anguilla / South Hill

South Hill villa

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.5 mi
  • Swimming pool
“British West Indies dream!!” My wife Joan and I arrived with our friends, Peter and Karen Hollander who live south of Boston, for a weeks stay in early april. We were greeted warmly by our hosts, the Louden's, who live in the villa next door. After s
…see more

Price per night from

$459

Responds fast!
avg. 3 hours 54 minutes

Price per night from

$459

Distance approx 7.42 km from Little Harbour Show on Map

21

Luxury studio 1 Sea view Orient bay

Saint-Martin / Orient Bay

Orient Bay studio

Studio 4 4 nights min

  • Studio
  • sleeps 4
  • 4 nights min
  • Child Friendly

Price per night from

$96

Price per night from

$96

Distance approx 6.32 km from Little Harbour Show on Map

(76) Excellent 

22

Luxury studio Sea View in Orient Bay

Saint-Martin / Orient Bay

Orient Bay apartment

1 4 4 nights min

  • 1 bedroom
  • sleeps 4
  • 4 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly
“Wonderful Vacation” We had a wonderful, relaxing vacation in a lovely condo nestled in Mt. Vernon. The owners Amaury & Thibault were very warm and when we had any questions, they answered them immediately. The whole condo was in great shape and the vi
…see more

Price per night from

$96

Price per night from

$96

Distance approx 10.8 km from Little Harbour Show on Map

15

Dawn Beach Resort, Westin Penthouse for 8 Guests!

Sint Maarten / Oyster Pond

Oyster Pond penthouse

3 8 7 nights min

  • 3 bedrooms
  • sleeps 8
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$492

Price per night from

$492

Distance approx 11.77 km from Little Harbour Show on Map

28

Gorgeous Beachfront Villa#9 at 'Villas on Great Bay'

Sint Maarten / Philipsburg

Philipsburg apartment

2 6 4 nights min

  • 2 bedrooms
  • sleeps 6
  • 4 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool

Price per night from

$386

Price per night from

$386

Distance approx 4.69 km from Little Harbour Show on Map

(16) Excellent 

63

LUXURY VILLA 'B ON THE SEA' IN ANGUILLA, 5 ENSUITE BEDROOMS, 2 DECKS, 2 POOLS

Anguilla

Anguilla villa

5 16 5 nights min

  • 5 bedrooms
  • sleeps 16
  • 5 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning
“No Place better than "B on the Sea"” This past year I was lucky enough to have the opportunity to stay at "B on the Sea" for a week vacation with friends. Besides the beauty of anguilla, the friendly locals, and the amazing food and drink, the accom
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Price per night from

$1,375

Price per night from

$1,375

Distance approx 10 km from Little Harbour Show on Map

20

The ONLY 5-Star on Dutch side: 3BR, 2BA, Full ktch

Sint Maarten / Oyster Pond

Oyster Pond apartment

3 8 7 nights min

  • 3 bedrooms
  • sleeps 8
  • 7 nights min
  • Child Friendly

Price per night from

$985

Price per night from

$985

Distance approx 9.68 km from Little Harbour Show on Map

5

safari on the beach

Saint-Martin / Marigot

Marigot apartment

1 4 4 nights min

  • 1 bedroom
  • sleeps 4
  • 4 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$173

Price per night from

$173

Distance approx 1.93 km from Little Harbour Show on Map

(4) Excellent 

32

NEW EXPANDED POOL & DECK! Oceanfront Beaches Edge East Villa

Anguilla / Blowing Point

Blowing Point villa

5 12 min stay varies

  • 5 bedrooms
  • sleeps 12
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.3 mi
  • Swimming pool

Price per night from

$1,401

Price per night from

$1,401

Distance approx 11.58 km from Little Harbour Show on Map

(1) Excellent 

9

Pelican Key 1Bedroom For Rent

Sint Maarten / Simpson Bay

Simpson Bay hotel apartment

1 4 4 nights min

  • 1 bedroom
  • sleeps 4
  • 4 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Ask about children

Price per night from

$265

Price per night from

$265

Distance approx 9.68 km from Little Harbour Show on Map

10

Villa Misty

Saint-Martin / Terres Basses

Terres Basses villa

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Swimming pool

Price per night from

$823

Responds fast!
avg. 3 hours 56 minutes

Price per night from

$823

Distance approx 2.56 km from Little Harbour Show on Map

(9) Excellent 

42

TRULY EFFORTLESS BEACH ACCESS! A MUST SEE! Alegria

Anguilla / Blowing Point

Blowing Point villa

4 12 min stay varies

  • 4 bedrooms
  • sleeps 12
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.2 mi
  • Swimming pool

Price per night from

$1,505

Price per night from

$1,505

Distance approx 10.96 km from Little Harbour Show on Map

(2)  

19

Coco Beach Duplex

Sint Maarten / Simpson Bay

Simpson Bay apartment

2 4 4 nights min

  • 2 bedrooms
  • sleeps 4
  • 4 nights min
  • Beach / lakeside relaxation
  • Child Friendly

Price per night from

$262

Price per night from

$262

Distance approx 10.81 km from Little Harbour Show on Map

7

Furnished apartment, cozy and comfortable, a perfect vacation experience

Sint Maarten / Cole Bay

Cole Bay apartment

1 3 7 nights min

  • 1 bedroom
  • sleeps 3
  • 7 nights min
  • Child Friendly

Price per night from

$97

Price per night from

$97

Distance approx 2.19 km from Little Harbour Show on Map

49

Award Winning Ocean Front Villa Estate

Anguilla

Anguilla house

9 10 min stay varies

  • 9 bedrooms
  • sleeps 10
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$7,220

Responds fast!
avg. 4 minutes

Price per night from

$7,220

Distance approx 9.63 km from Little Harbour Show on Map

7

Friends Villa

Saint-Martin / Terres Basses

Terres Basses villa

12 26 1 night min

  • 12 bedrooms
  • sleeps 26
  • 1 night min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$8,015

Price per night from

$8,015

Distance approx 1.93 km from Little Harbour Show on Map

13

Champagne Shores Villa

Anguilla / Blowing Point

Blowing Point villa

5 10 4 nights min

  • 5 bedrooms
  • sleeps 10
  • 4 nights min
  • Nearest beach 0 mi
  • Swimming pool
  • Child Friendly

Price per night from

$1,953

Price per night from

$1,953

Distance approx 12.33 km from Little Harbour Show on Map

38

Divi LIttle Bay Beach St Maarten Studio 1BA Suite

Sint Maarten / Philipsburg

Philipsburg apartment

2 2 7 nights min

  • 2 bedrooms
  • sleeps 2
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool

Price per night from

$172

Responds fast!
avg. 59 minutes

Price per night from

$172

Distance approx 9.74 km from Little Harbour Show on Map

8

Studio Baie Nettle in the hotel complex "Les Flamboyants"

Saint-Martin / Baie Nettle

Baie Nettle studio

Studio 4 2 nights min

  • Studio
  • sleeps 4
  • 2 nights min
  • Child Friendly

Price per night from

$92

Price per night from

$92

Distance approx 8.21 km from Little Harbour Show on Map

5

GRYSTONE

Saint-Martin / Terres Basses

Terres Basses villa

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Air conditioning
Inquire for Rates
Inquire for Rates

Distance approx 10.94 km from Little Harbour Show on Map

(10) Excellent 

17

Paradise Found at Las Arenas - Beachfront Luxury!

Sint Maarten / Simpson Bay

Simpson Bay apartment

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
“Amazing place - all the owner says it is, and more!” This was our first trip to St. Maarten so we had no idea what kind of places were available or what 'neighborhood' was best to stay in. I've got to say that we really lucked-out in choosing 'Paradis
…see more

Price per night from

$410

Price per night from

$410

Distance approx 8.95 km from Little Harbour Show on Map

(1)  

11

Villa Les Jardins de Bllevue

Saint-Martin / Marigot, Saint Martin

Marigot, Saint Martin villa

6 12 5 nights min

  • 6 bedrooms
  • sleeps 12
  • 5 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

Price per night from

$1,838

Price per night from

$1,838

Distance approx 10.57 km from Little Harbour Show on Map

17

 Villa Cyrano, lowland, Saint Martin.

Saint-Martin / Terres Basses

Terres Basses villa

3 6 6 nights min

  • 3 bedrooms
  • sleeps 6
  • 6 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$771

Price per night from

$771

Distance approx 9.03 km from Little Harbour Show on Map

22

Villa Madeira

Saint-Martin / Marigot

Marigot villa

4 2 3 nights min

  • 4 bedrooms
  • sleeps 2
  • 3 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$1,081

Responds fast!
avg. 2 hours 43 minutes

Price per night from

$1,081