Simpson Bay Beach Rentals

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1,734 Houses

(4) Excellent 

10

2BR-Oceanfront-Royal Palm

Simpson Bay / Simpson Bay Beach

Simpson Bay condo

2 6 5 nights min

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

Price per night from

$401

Price per night from

$401

(5) Excellent 

26

Le Papillon - REOPENED AFTER IRMA - Modern Beachfront Unit with great view

Simpson Bay / Simpson Bay Beach

Simpson Bay apartment

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.01 mi
  • Child Friendly

Price per night from

$325

Responds fast!
avg. 1 hour 55 minutes

Price per night from

$325

(4) Very Good 

12

PELICAN KEY - CHARMING STUDIO WITH OCEAN VIEW

Simpson Bay / Simpson Bay Beach

Simpson Bay apartment

1 2 4 nights min

  • 1 bedroom
  • sleeps 2
  • 4 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.8 mi
  • Air conditioning

Price per night from

$121

Responds fast!
avg. 3 hours 41 minutes

Price per night from

$121

(1) Excellent 

34

Caribbean Sun

Simpson Bay / Simpson Bay Beach

Simpson Bay condo

2 4 6 nights min

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

Price per night from

$300

Responds fast!
avg. 2 hours 24 minutes

Price per night from

$300

17

Pearl on the Beach

Simpson Bay / Simpson Bay Beach

Simpson Bay condo

2 4 5 nights min

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

Price per night from

$516

Price per night from

$516

32

Barefoot Oceanfront Condo St Maarten

Simpson Bay / Simpson Bay Beach

Simpson Bay villa

2 6 4 nights min

  • 2 bedrooms
  • sleeps 6
  • 4 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$305

Price per night from

$305

9

Beachfront Condo

Simpson Bay / Simpson Bay Beach

Simpson Bay condo

2 4 5 nights min

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

Price per night from

$515

Price per night from

$515

(2) Excellent 

18

Anchorage Apartment

Simpson Bay / Simpson Bay Beach

Simpson Bay apartment

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 2 mi
  • Child Friendly

Price per night from

$160

Responds fast!
avg. 2 hours 17 minutes

Price per night from

$160

(1) Excellent 

26

Vacation Villa at Simpson's bay and Marina

Simpson Bay / Simpson Bay Beach

Simpson Bay villa

1 4 7 nights min

  • 1 bedroom
  • sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.2 mi
  • Swimming pool

Price per night from

$136

Responds fast!
avg. 1 hour 33 minutes

Price per night from

$136

(1)  

5

Beach Heaven

Simpson Bay / Simpson Bay Beach

Simpson Bay penthouse

2 4 1 night min

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

Price per night from

$344

Price per night from

$344

Great rentals within 20 miles that match your search

Distance approx 2.82 km from Simpson Bay Beach Show on Map

(7) Excellent 

35

Exclusive and private Caribbean Guesthouse

Saint-Martin / Terres Basses

Terres Basses villa

3 6 2 nights min

  • 3 bedrooms
  • sleeps 6
  • 2 nights min
  • Nearest beach 2 mi
  • Swimming pool
  • Child Friendly
“It's just a paradise!” We stayed in this beautiful guest house for a few days, but soon felt so much "at home" that it we didn't want to leave and get back to reality any more... ;) The owners are very warm, welcoming, responsive to all needs and alw
…see more

Price per night from

$200

Price per night from

$200

Distance approx 5.28 km from Simpson Bay Beach Show on Map

(2) Excellent 

29

NEW & CENTRAL Apartment on the Grand Case Beach. Pool, Parking. Kind Size Bed.

Saint-Martin / Grand Case

Grand Case apartment

1 4 5 nights min

  • 1 bedroom
  • sleeps 4
  • 5 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool

Price per night from

$266

Responds fast!
avg. 2 hours 42 minutes

Price per night from

$266

Distance approx 9.56 km from Simpson Bay Beach Show on Map

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

$450

Price per night from

$450

Distance approx 15.32 km from Simpson Bay Beach Show on Map

(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

Responds fast!
avg. 3 hours 27 minutes

Price per night from

$100

Distance approx 5.47 km from Simpson Bay Beach 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

$428

Price per night from

$428

Distance approx 19.79 km from Simpson Bay Beach Show on Map

26

Villa Eden Island, 3 bedroom

St. Barthelemy / Gustavia

Gustavia villa

3 6 5 nights min

  • 3 bedrooms
  • sleeps 6
  • 5 nights min
  • Nearest beach 0.5 mi
  • Swimming pool
  • Ask about children

Price per night from

$857

Price per night from

$857

Distance approx 5.07 km from Simpson Bay Beach Show on Map

35

Villa Robinson. Breathtaking view!

Sint Maarten / Oyster Pond

Oyster Pond villa

3 8 2 nights min

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

Price per night from

$1,032

Price per night from

$1,032

Distance approx 16.73 km from Simpson Bay Beach Show on Map

(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

Distance approx 2.43 km from Simpson Bay Beach Show on Map

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

$450

Responds fast!
avg. 41 minutes

Price per night from

$450

Distance approx 9.8 km from Simpson Bay Beach Show on Map

4

Gardenia Villa at Indigo Reef

Anguilla / The Valley

The Valley villa

1 2 4 nights min

  • 1 bedroom
  • sleeps 2
  • 4 nights min
  • Nearest beach 0.9 mi
  • Child Friendly
  • Pet Friendly

Price per night from

$325

Price per night from

$325

Distance approx 6.42 km from Simpson Bay Beach Show on Map

17

Emmas Beach Studio 4316

Saint-Martin / Orient Bay

Orient Bay studio

Studio 4 5 nights min

  • Studio
  • sleeps 4
  • 5 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool

Price per night from

$140

Price per night from

$140

Distance approx 5.67 km from Simpson Bay Beach Show on Map

9

Oyster Bay Beach Resort

Sint Maarten / Philipsburg

Philipsburg condo

1 4 7 nights min

  • 1 bedroom
  • sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$243

Responds fast!
avg. 2 hours 37 minutes

Price per night from

$243

Distance approx 5.44 km from Simpson Bay Beach Show on Map

(10) Excellent 

37

Beachfront home featured on HGTV 5 bedrooms, pool

Sint Maarten / Philipsburg

Philipsburg villa

5 20 3 nights min

  • 5 bedrooms
  • sleeps 20
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.25 mi
  • Swimming pool

Price per night from

$899

Price per night from

$899

Distance approx 1.38 km from Simpson Bay Beach Show on Map

11

Villa Blue Lagoon SXM

Sint Maarten / Maho

Maho villa

5 10 7 nights min

  • 5 bedrooms
  • sleeps 10
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$1,430

Price per night from

$1,430

Distance approx 15.6 km from Simpson Bay Beach Show on Map

30

Allamanda Beach Club - Ground Floor Deluxe Apartment #1

Anguilla / The Valley

The Valley house

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Swimming pool
  • Car not necessary
  • Air conditioning

Price per night from

$276

Responds fast!
avg. 2 hours 46 minutes

Price per night from

$276

Distance approx 9.92 km from Simpson Bay Beach Show on Map

36

Luxurious and Exclusive Beachfront Property

Anguilla / West End Village

West End Village villa

9 18 min stay varies

  • 9 bedrooms
  • sleeps 18
  • min stay varies
  • Swimming pool
  • Air conditioning

Price per night from

$14,286

Responds fast!
avg. 3 minutes

Price per night from

$14,286

Distance approx 1.99 km from Simpson Bay Beach Show on Map

4

Jacqueline's 3BDR Guest House

Saint-Martin / Marigot

Marigot guest house

3 9 3 nights min

  • 3 bedrooms
  • sleeps 9
  • 3 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$148

Responds fast!
avg. 3 hours 11 minutes

Price per night from

$148

Distance approx 15.6 km from Simpson Bay Beach Show on Map

10

Allamanda Beach Club - 2nd Floor Deluxe Queen #1

Anguilla / The Valley

The Valley house

1 4 2 nights min

  • 1 bedroom
  • sleeps 4
  • 2 nights min
  • Swimming pool
  • Car not necessary
  • Air conditioning

Price per night from

$297

Responds fast!
avg. 2 hours 46 minutes

Price per night from

$297

Distance approx 9.67 km from Simpson Bay Beach Show on Map

(3) Excellent 

22

Anguilla Bow Green Villa on Rendezvous Bay Beach

Anguilla / West End Village

West End Village villa

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$1,093

Price per night from

$1,093

Distance approx 1 km from Simpson Bay Beach Show on Map

4

Oceanfront Townhouse in Pelican Key

Sint Maarten / Philipsburg

Philipsburg townhouse

3 6 5 nights min

  • 3 bedrooms
  • sleeps 6
  • 5 nights min
  • Child Friendly
  • Air conditioning

Price per night from

$295

Price per night from

$295

Distance approx 9.43 km from Simpson Bay Beach Show on Map

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

$1,200

Responds fast!
avg. 1 hour 49 minutes

Price per night from

$1,200

Distance approx 15.09 km from Simpson Bay Beach Show on Map

(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

Responds fast!
avg. 1 hour 49 minutes

Price per night from

$149

Distance approx 5.43 km from Simpson Bay Beach Show on Map

9

COME SPEND HOLIDAY SUPER FACING THE SEA

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

$491

Price per night from

$491

Distance approx 1.71 km from Simpson Bay Beach Show on Map

9

Studio private beach in Marigot

Saint-Martin / Marigot

Marigot apartment

1 2 3 nights min

  • 1 bedroom
  • sleeps 2
  • 3 nights min
  • Child Friendly

Price per night from

$69

Responds fast!
avg. 1 hour 30 minutes

Price per night from

$69

Distance approx 5.7 km from Simpson Bay Beach Show on Map

(1) Excellent 

24

EDEN ROCK beautiful villa with stunning views

Saint-Martin / Oyster Pond

Oyster Pond villa

5 10 7 nights min

  • 5 bedrooms
  • sleeps 10
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$717

Responds fast!
avg. 2 hours 8 minutes

Price per night from

$717

Distance approx 5.71 km from Simpson Bay Beach Show on Map

11

Beautiful apartment on St Martin

Sint Maarten / Oyster Pond

Oyster Pond apartment

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly
Inquire for Rates
Inquire for Rates

Distance approx 5.92 km from Simpson Bay Beach Show on Map

(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

$424

Price per night from

$424

Distance approx 18.43 km from Simpson Bay Beach Show on Map

14

Villa Datcha

St. Barthelemy / Anse des Flamands

Anse des Flamands villa

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Nearest beach 1 mi
  • Swimming pool
  • Air conditioning

Price per night from

$866

Responds fast!
avg. 2 hours 9 minutes

Price per night from

$866