Island Harbour Rentals

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1,275 Houses

(1) Excellent 

10

Wesley House - Anguilla

Anguilla / Island Harbour

Island Harbour house

3 6 1 night min

  • 3 bedrooms
  • sleeps 6
  • 1 night min
  • Swimming pool
  • Ask about children
  • Air conditioning

Price per night from

$964

Price per night from

$964

(13) Very Good 

24

James Place Apartments, Anguilla , British West Indies

Anguilla / Island Harbour

Island Harbour apartment

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 8 mi
  • Child Friendly

Price per night from

$100

Price per night from

$100

10

Kiki Villa - Anguilla

Anguilla / Island Harbour

Island Harbour house

4 8 1 night min

  • 4 bedrooms
  • sleeps 8
  • 1 night min
  • Swimming pool
  • Ask about children
  • Ask about pets

Price per night from

$800

Price per night from

$800

(8) Very Good 

31

Ocean View Apartment at Captain's Ridge (view from every room)

Anguilla / Island Harbour

Island Harbour apartment

2 4 3 nights min

  • 2 bedrooms
  • sleeps 4
  • 3 nights min
  • Nearest beach 3 mi
  • Air conditioning
  • Private garden

Price per night from

$120

Price per night from

$120

10

Yellow Villa - Anguilla

Anguilla / Island Harbour

Island Harbour house

5 10 1 night min

  • 5 bedrooms
  • sleeps 10
  • 1 night min
  • Swimming pool
  • Ask about children
  • Ask about pets

Price per night from

$2,500

Price per night from

$2,500

13

Ultimacy

Anguilla / Island Harbour

Island Harbour villa

8 16 min stay varies

  • 8 bedrooms
  • sleeps 16
  • min stay varies
  • Child Friendly

Price per night from

$4,000

Price per night from

$4,000

(3) Excellent 

32

Villa Amarilla

Anguilla / Island Harbour

Island Harbour villa

5 10 min stay varies

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

Price per night from

$2,500

Responds fast!
avg. 1 hour 32 minutes

Price per night from

$2,500

29

Villa Amarilla

Anguilla / Island Harbour

Island Harbour villa

5 10 min stay varies

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

Price per night from

$2,500

Price per night from

$2,500

32

Villa Amarilla

Anguilla / Island Harbour

Island Harbour villa

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Ask about children
  • Ask about pets

Price per night from

$2,100

Responds fast!
avg. 1 hour 32 minutes

Price per night from

$2,100

32

Villa Amarilla

Anguilla / Island Harbour

Island Harbour villa

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Ask about children
  • Ask about pets

Price per night from

$2,300

Responds fast!
avg. 1 hour 32 minutes

Price per night from

$2,300

10

Quixotic Villas - Anguilla

Anguilla / Island Harbour

Island Harbour house

4 8 1 night min

  • 4 bedrooms
  • sleeps 8
  • 1 night min
  • Swimming pool
  • Ask about children
  • Ask about pets

Price per night from

$575

Price per night from

$575

(59) Excellent 

38

COUPLES ONLY RETREAT - Stunning Panoramic Ocean Views - Private Pool

Anguilla / Island Harbour

Island Harbour villa

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 1 mi
  • Swimming pool
“Perfect & Peaceful!” There are not too many other positive things I can say about Almond Tree Villa that has not already been mentioned by other reviewers. However, with that being said, if you are considering a stay at Joe & Sue's wonderful retreat,
…see more

Price per night from

$350

Price per night from

$350

19

Villa Azure

Anguilla / Island Harbour

Island Harbour villa

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Ask about children
  • Ask about pets

Price per night from

$1,475

Responds fast!
avg. 1 hour 32 minutes

Price per night from

$1,475

19

Villa Azure

Anguilla / Island Harbour

Island Harbour villa

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Ask about children
  • Ask about pets

Price per night from

$1,675

Responds fast!
avg. 1 hour 32 minutes

Price per night from

$1,675

19

Villa Azure

Anguilla / Island Harbour

Island Harbour villa

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Ask about children
  • Ask about pets

Price per night from

$1,475

Responds fast!
avg. 1 hour 32 minutes

Price per night from

$1,475

19

Villa Azure

Anguilla / Island Harbour

Island Harbour villa

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
  • Ask about children
  • Ask about pets

Price per night from

$1,375

Responds fast!
avg. 1 hour 32 minutes

Price per night from

$1,375

25

Luxury Villa All Suites Great for Families and Couples

Anguilla / Island Harbour

Island Harbour villa

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 3 mi
  • Swimming pool

Price per night from

$870

Responds fast!
avg. 3 hours 10 minutes

Price per night from

$870

37

Beachcourt Villa

Anguilla / Island Harbour

Island Harbour villa

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Ask about children
  • Ask about pets

Price per night from

$1,100

Responds fast!
avg. 1 hour 32 minutes

Price per night from

$1,100

37

Beachcourt Villa

Anguilla / Island Harbour

Island Harbour villa

7 14 min stay varies

  • 7 bedrooms
  • sleeps 14
  • min stay varies
  • Ask about children
  • Ask about pets

Price per night from

$1,875

Responds fast!
avg. 1 hour 32 minutes

Price per night from

$1,875

37

Beachcourt Villa

Anguilla / Island Harbour

Island Harbour villa

8 16 min stay varies

  • 8 bedrooms
  • sleeps 16
  • min stay varies
  • Ask about children
  • Ask about pets

Price per night from

$2,075

Responds fast!
avg. 1 hour 32 minutes

Price per night from

$2,075

37

Beachcourt Villa

Anguilla / Island Harbour

Island Harbour villa

6 12 min stay varies

  • 6 bedrooms
  • sleeps 12
  • min stay varies
  • Ask about children
  • Ask about pets

Price per night from

$1,650

Responds fast!
avg. 1 hour 32 minutes

Price per night from

$1,650

37

Beachcourt Villa

Anguilla / Island Harbour

Island Harbour villa

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Ask about children
  • Ask about pets

Price per night from

$1,400

Responds fast!
avg. 1 hour 32 minutes

Price per night from

$1,400

33

Romeo Villa Anguilla

Anguilla / Island Harbour

Island Harbour villa

7 16 min stay varies

  • 7 bedrooms
  • sleeps 16
  • min stay varies
  • Nearest beach 1 mi
  • Swimming pool
  • Child Friendly

Price per night from

$1,550

Price per night from

$1,550

(1) Average 

43

CATALINA VILLA AT SHOAL BAY EAST

Anguilla / Island Harbour

Island Harbour villa

2 5 4 nights min

  • 2 bedrooms
  • sleeps 5
  • 4 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$149

Price per night from

$149

Great rentals within 20 miles that match your search

Distance approx 11.18 km from Island Harbour

13

New studio sea view at Mont Vernon Residence

Saint-Martin / Orient Bay

Orient Bay studio

Studio 2 5 nights min

  • Studio
  • sleeps 2
  • 5 nights min
  • Child Friendly
  • Air conditioning

Price per night from

$70

Price per night from

$70

Distance approx 16.16 km from Island Harbour

35

Villa Madeleine

Saint-Martin / Terres Basses

Terres Basses villa

7 14 min stay varies

  • 7 bedrooms
  • sleeps 14
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$1,368

Responds fast!
avg. 3 hours 58 minutes

Price per night from

$1,368

Distance approx 15.36 km from Island Harbour

20

Villa Friends

Saint-Martin / Terres Basses

Terres Basses villa

14 30 1 night min

  • 14 bedrooms
  • sleeps 30
  • 1 night min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$5,337

Price per night from

$5,337

Distance approx 16.59 km from Island Harbour

9

Modern Blue Residence Condo, Cupecoy, Sint Maarten

Sint Maarten / Philipsburg

Philipsburg apartment

2 6 3 nights min

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

Price per night from

$448

Price per night from

$448

Distance approx 9.25 km from Island Harbour

30

Sea Villa on Long Bay Beach: Sugar Sand Beach, Pool, Hot Tub, Butler, Concierge.

Anguilla / Long Bay Village

Long Bay Village villa

6 11 min stay varies

  • 6 bedrooms
  • sleeps 11
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$3,275

Price per night from

$3,275

Distance approx 15.36 km from Island Harbour

19

Coconut Villa

Saint-Martin / Terres Basses

Terres Basses villa

2 4 1 night min

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

Price per night from

$349

Price per night from

$349

Distance approx 16.75 km from Island Harbour

14

JUNIOR SUITE SIMPSON BAY RESORT & MARINA 1BR 1BA 2pers

Sint Maarten / Simpson Bay

Simpson Bay apartment

1 2 7 nights min

  • 1 bedroom
  • sleeps 2
  • 7 nights min
  • Swimming pool
  • Air conditioning

Price per night from

$100

Responds fast!
avg. 3 hours 1 minutes

Price per night from

$100

Distance approx 14.36 km from Island Harbour

21

Villa Madeira

Saint-Martin / Marigot

Marigot villa

4 8 min stay varies

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

Price per night from

$936

Responds fast!
avg. 3 hours 58 minutes

Price per night from

$936

Distance approx 15.36 km from Island Harbour

12

Bonanza Villa

Saint-Martin / Terres Basses

Terres Basses villa

4 8 1 night min

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

Price per night from

$1,228

Price per night from

$1,228

Distance approx 11.22 km from Island Harbour

14

Villa Mariana

Saint-Martin / Grand Case

Grand Case villa

3 6 min stay varies

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

Price per night from

$522

Responds fast!
avg. 3 hours 58 minutes

Price per night from

$522

Distance approx 11.24 km from Island Harbour

12

New studio in Mont Vernon sea view

Saint-Martin / Orient Bay

Orient Bay studio

Studio 3 5 nights min

  • Studio
  • sleeps 3
  • 5 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$68

Price per night from

$68

Distance approx 11.71 km from Island Harbour

(1) Excellent 

30

Eve Paradise Villa - Orient Bay - St Martin French Antilles

Saint-Martin / Marigot

Marigot villa

4 8 5 nights min

  • 4 bedrooms
  • sleeps 8
  • 5 nights min
  • Child Friendly

Price per night from

$419

Price per night from

$419

Distance approx 11.21 km from Island Harbour

14

Villa Mariana

Saint-Martin / Grand Case

Grand Case villa

3 6 min stay varies

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

Price per night from

$521

Responds fast!
avg. 2 hours 32 minutes

Price per night from

$521

Distance approx 12.36 km from Island Harbour

14

Nice apt with terrace & Wifi

Saint-Martin / La Savane

La Savane apartment

1 4 1 night min

  • 1 bedroom
  • sleeps 4
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 3 mi
  • Child Friendly

Price per night from

$142

Price per night from

$142