Top 50 Leeward Settlement Vacation Rentals

Villas (424)
Condos (233)
Houses (111)
Golf rental (540)
Beachfront (396)
Ocean view (344)

Explore a selection of Leeward Settlement vacation rentals

Columbus Cottage, Sleeps 4/5, Good Pool, Private Garden; very...
Guests5
Bedrooms2
Bathrooms2
Wonderful 4.9 / 5
$310 avg/night
2 beds
2 Bathrooms
Guests 5
33 reviews
Fantastic family villa, sleeps 8-10, 4 bedrooms, 2 pool, BBQ Pit...
Guests11
Bedrooms4
Bathrooms4
Wonderful 5 / 5
$1,200 avg/night
4 beds
4 Bathrooms
Guests 11
50 reviews
Villa Tropica | Luxury Villa Near Beach, Lush Garden, Chromatic...
Guests12
Bedrooms5
Bathrooms4
Wonderful 4.9 / 5
$625 avg/night
5 beds
4 Bathrooms
Guests 12
56 reviews
'Barefoot Palms' **Sept thru Nov 1, stay 9 pay for 7**
Guests6
Bedrooms3
Bathrooms2
Wonderful 5 / 5
$380 avg/night
3 beds
2 Bathrooms
Guests 6
33 reviews
Modern Luxury Grace Bay Condo -Amazing Rates
Guests5
Bedrooms2
Bathrooms2
Wonderful 5 / 5
$240 avg/night
2 beds
2 Bathrooms
Guests 5
30 reviews
Charming Garden Cottage in Leeward
Guests3
Bedroom1
Bathroom1
Wonderful 5 / 5
$159 avg/night
1 bed
1 Bathroom
Guests 3
29 reviews
Turks and Caicos Island, Grace Bay Beach, Brand New Villa
Guests6
Bedrooms2
Bathrooms2
Wonderful 4.8 / 5
$521 avg/night
2 beds
2 Bathrooms
Guests 6
7 reviews
Charming private cottage few minutes walk to famous Grace Bay...
Guests4
Bedrooms3
Bathrooms0
Wonderful 4.4 / 5
$183 avg/night
3 beds
0 Bathrooms
Guests 4
23 reviews
New to the Market -- Relax in your own paradise
Guests6
Bedrooms3
Bathrooms3
Wonderful 0 / 5
$500 avg/night
3 beds
3 Bathrooms
Guests 6
Tranquility Lane Beachfront Cottage
Guests4
Bedroom1
Bathroom1
Wonderful 5 / 5
$517 avg/night
1 bed
1 Bathroom
Guests 4
1 reviews
Villa Kendara- Seafront Luxe Apt- Great Views & Amenities- SALE...
Guests3
Bedroom1
Bathroom1
Wonderful 4.9 / 5
$145 avg/night
1 bed
1 Bathroom
Guests 3
71 reviews
Brand New Shore Club Guest House!!
Guests4
Bedrooms2
Bathroom1
Wonderful 5 / 5
$348 avg/night
2 beds
1 Bathroom
Guests 4
1 reviews
FOOTPRINTS VILLA. A STUNNING GRACE BAY BEACHFRONT HOME, INCLUDING...
Guests12
Bedrooms5
Bathrooms5
Wonderful 5 / 5
$2,564 avg/night
5 beds
5 Bathrooms
Guests 12
71 reviews
Picture Perfect Brand New 5 Bed Villa in Grace Bay. Housekeeping...
Guests10
Bedrooms5
Bathrooms5
Wonderful 5 / 5
$1,800 avg/night
5 beds
5 Bathrooms
Guests 10
3 reviews
Sunset Beach Villas - Turnstone House - Brand new! Housekeeping...
Guests6
Bedrooms3
Bathrooms3
Wonderful 0 / 5
$1,474 avg/night
3 beds
3 Bathrooms
Guests 6
4 bd. family friendly villa, steps to Grace Bay Beach, pool, beach...
Guests8
Bedrooms4
Bathroom1
Wonderful 0 / 5
$2,751 avg/night
4 beds
1 Bathroom
Guests 8
Luxury Beachfront Villa with Ocean Views over Grace Bay
Guests8
Bedrooms4
Bathrooms4
Wonderful 0 / 5
$2,782 avg/night
4 beds
4 Bathrooms
Guests 8
Enjoy Late Summer Specials at 1 of our most popular beachfront...
Guests9
Bedrooms4
Bathrooms4
Wonderful 5 / 5
$1,271 avg/night
4 beds
4 Bathrooms
Guests 9
1 reviews
*SPECIAL OFFERS JUST ASK*- CONCH VILLA GRACE BAY - Luxury Beach...
Guests6
Bedrooms3
Bathrooms4
Wonderful 5 / 5
$2,650 avg/night
3 beds
4 Bathrooms
Guests 6
2 reviews
ENJOY 40% Off Sept. - October, 2017: E102 - Our Beautiful...
Guests6
Bedrooms3
Bathrooms3
Wonderful 5 / 5
$1,084 avg/night
3 beds
3 Bathrooms
Guests 6
2 reviews
*FREE CAR RENTAL* - Luxury Ocean Front Villa on Grace Bay - ACCESS...
Guests8
Bedrooms3
Bathrooms3
Wonderful 0 / 5
$1,224 avg/night
3 beds
3 Bathrooms
Guests 8
2 villas for rent in long bay, private pool, kite, 5 minute walk...
Guests12
Bedrooms4
Bathrooms3
Wonderful 4.8 / 5
$266 avg/night
4 beds
3 Bathrooms
Guests 12
6 reviews
Privacy and luxury on a magnificent powder sand beach
Guests8
Bedrooms4
Bathrooms4
Wonderful 0 / 5
$1,251 avg/night
4 beds
4 Bathrooms
Guests 8
*CONTACT US AT EXCEPTIONAL VILLAS FOR BEST OFFER* Amazing Beach...
Guests10
Bedrooms5
Bathrooms6
Wonderful 5 / 5
$5,707 avg/night
5 beds
6 Bathrooms
Guests 10
2 reviews
*SPECIAL OFFERS JUST ASK*- CONCH VILLA GRACE BAY - Luxury Beach...
Guests8
Bedrooms4
Bathrooms5
Wonderful 0 / 5
$2,392 avg/night
4 beds
5 Bathrooms
Guests 8
Coral House Turks And Caicos Oceanfront Estate
Guests10
Bedrooms5
Bathrooms5
Wonderful 0 / 5
$5,917 avg/night
5 beds
5 Bathrooms
Guests 10
Saving Grace - Leeward Settlement
Guests8
Bedrooms4
Bathrooms4
Wonderful 0 / 5
$2,843 avg/night
4 beds
4 Bathrooms
Guests 8
Luxury Grace Bay Villa with Ocean Views and Private Beach
Guests6
Bedrooms3
Bathrooms3
Wonderful 0 / 5
$2,250 avg/night
3 beds
3 Bathrooms
Guests 6
*CONTACT US DIRECTLY AT EXCEPTIONAL VILLAS FOR BEST OFFER*Amazing...
Guests10
Bedrooms5
Bathrooms6
Wonderful 0 / 5
$5,151 avg/night
5 beds
6 Bathrooms
Guests 10
Contemporary beach front villa at Grace Bay beach
Guests8
Bedrooms4
Bathrooms4
Wonderful 0 / 5
$2,615 avg/night
4 beds
4 Bathrooms
Guests 8
Hawksbill - Leeward Settlement
Guests16
Bedrooms8
Bathrooms8
Wonderful 0 / 5
$11,313 avg/night
8 beds
8 Bathrooms
Guests 16
Modern Designer Turks and Caicos Luxury Beachfront Villa with Pool
Guests16
Bedrooms8
Bathrooms8
Wonderful 0 / 5
$11,497 avg/night
8 beds
8 Bathrooms
Guests 16
Coral House - T&amp;C
Guests10
Bedrooms5
Bathrooms5
Wonderful 0 / 5
$5,212 avg/night
5 beds
5 Bathrooms
Guests 10
Saving Grace Villa Turks and Caicos Estate
Guests8
Bedrooms4
Bathrooms3
Wonderful 0 / 5
$2,750 avg/night
4 beds
3 Bathrooms
Guests 8
Two story colonial styled villa
Guests8
Bedrooms4
Bathrooms4
Wonderful 0 / 5
$2,864 avg/night
4 beds
4 Bathrooms
Guests 8
Beach House at Hawksbill
Guests4
Bedrooms2
Bathrooms2
Wonderful 0 / 5
$1,452 avg/night
2 beds
2 Bathrooms
Guests 4
Welcome To The Seashell Breeze Villa, Turks And Caicos Islands!
Guests4
Bedrooms2
Bathroom1
Wonderful 5 / 5
$230 avg/night
2 beds
1 Bathroom
Guests 4
52 reviews
2 Bed home one road back from Grace Bay Beach
Guests6
Bedrooms2
Bathrooms2
Wonderful 4.2 / 5
$273 avg/night
2 beds
2 Bathrooms
Guests 6
11 reviews
Designer Villa near Pelican Beach, Waterslide, Bicycles, Kayaks...
Guests12
Bedrooms5
Bathrooms4
Wonderful 4.9 / 5
$600 avg/night
5 beds
4 Bathrooms
Guests 12
10 reviews
1 Bedroom Bungalow 250m from beach (sleeps 4)
Guests4
Bedroom1
Bathroom1
Wonderful 4.6 / 5
$159 avg/night
1 bed
1 Bathroom
Guests 4
28 reviews
Pelican Nest,Cocoa Villa-6 acres on Grace Bay Beach-20% off...
Guests7
Bedrooms3
Bathrooms4
Wonderful 4.8 / 5
$786 avg/night
3 beds
4 Bathrooms
Guests 7
6 reviews
Cozy Beach House 2 on Kite Boarding Beach.
Guests6
Bedrooms3
Bathroom1
Wonderful 4.8 / 5
$379 avg/night
3 beds
1 Bathroom
Guests 6
40 reviews
Affordable Luxury Leeward near Pelican Beach, Grace Bay, Hot Tub...
Guests8
Bedrooms4
Bathrooms3
Wonderful 4.9 / 5
$1,518 avg/night
4 beds
3 Bathrooms
Guests 8
18 reviews
Newly Renovated 8 Bedroom 7 Bath Villa Spectacular Views Ocean...
Guests20
Bedrooms8
Bathrooms7
Wonderful 5 / 5
$586 avg/night
8 beds
7 Bathrooms
Guests 20
6 reviews
Brand New Waterfront Luxury Villa With Views!!
Guests8
Bedrooms4
Bathrooms4
Wonderful 5 / 5
$600 avg/night
4 beds
4 Bathrooms
Guests 8
8 reviews
Large Waterfront Villa 3 King and 1 Twin Bedroom - Kayaks, SUPs...
Guests9
Bedrooms4
Bathrooms3
Wonderful 4.9 / 5
$918 avg/night
4 beds
3 Bathrooms
Guests 9
14 reviews
Cozy Beach House on Kite Boarding Beach,W/Private Pool and kayak.
Guests6
Bedrooms3
Bathroom1
Wonderful 4.7 / 5
$376 avg/night
3 beds
1 Bathroom
Guests 6
51 reviews
Beauty and the Beach!
Guests4
Bedrooms2
Bathrooms2
Wonderful 5 / 5
$320 avg/night
2 beds
2 Bathrooms
Guests 4
6 reviews
10% OFF Until Dec 15!! 10 Steps to Grace Bay Beach, , 4BR...
Guests8
Bedrooms4
Bathrooms2
Wonderful 5 / 5
$495 avg/night
4 beds
2 Bathrooms
Guests 8
7 reviews
Pelican Cottage - Minutes to Grace Bay Beach!!Bikes Incuded!!/Car...
Guests2
Bedroom1
Bathroom1
Wonderful 5 / 5
$121 avg/night
1 bed
1 Bathroom
Guests 2
7 reviews

Leeward Settlement, Turks and Caicos Islands Vacation Rentals

Columbus Cottage, Sleeps 4/5, Good Pool, Private Garden; very...

Fantastic family villa, sleeps 8-10, 4 bedrooms, 2 pool, BBQ Pit...

Villa Tropica | Luxury Villa Near Beach, Lush Garden, Chromatic...

'Barefoot Palms' **Sept thru Nov 1, stay 9 pay for 7**

Modern Luxury Grace Bay Condo -Amazing Rates

Charming Garden Cottage in Leeward

Turks and Caicos Island, Grace Bay Beach, Brand New Villa

Charming private cottage few minutes walk to famous Grace Bay...

New to the Market -- Relax in your own paradise

Tranquility Lane Beachfront Cottage

Villa Kendara- Seafront Luxe Apt- Great Views & Amenities- SALE...

Brand New Shore Club Guest House!!

FOOTPRINTS VILLA. A STUNNING GRACE BAY BEACHFRONT HOME, INCLUDING...

Picture Perfect Brand New 5 Bed Villa in Grace Bay. Housekeeping...

Sunset Beach Villas - Turnstone House - Brand new! Housekeeping...

4 bd. family friendly villa, steps to Grace Bay Beach, pool, beach...

Luxury Beachfront Villa with Ocean Views over Grace Bay

Enjoy Late Summer Specials at 1 of our most popular beachfront...

*SPECIAL OFFERS JUST ASK*- CONCH VILLA GRACE BAY - Luxury Beach...

ENJOY 40% Off Sept. - October, 2017: E102 - Our Beautiful...

*FREE CAR RENTAL* - Luxury Ocean Front Villa on Grace Bay - ACCESS...

2 villas for rent in long bay, private pool, kite, 5 minute walk...

Privacy and luxury on a magnificent powder sand beach

*CONTACT US AT EXCEPTIONAL VILLAS FOR BEST OFFER* Amazing Beach...

*SPECIAL OFFERS JUST ASK*- CONCH VILLA GRACE BAY - Luxury Beach...

Coral House Turks And Caicos Oceanfront Estate

Saving Grace - Leeward Settlement

Luxury Grace Bay Villa with Ocean Views and Private Beach

*CONTACT US DIRECTLY AT EXCEPTIONAL VILLAS FOR BEST OFFER*Amazing...

Contemporary beach front villa at Grace Bay beach

Hawksbill - Leeward Settlement

Modern Designer Turks and Caicos Luxury Beachfront Villa with Pool

Coral House - T&amp;amp;C

Saving Grace Villa Turks and Caicos Estate

Two story colonial styled villa

Beach House at Hawksbill

Welcome To The Seashell Breeze Villa, Turks And Caicos Islands!

2 Bed home one road back from Grace Bay Beach

Designer Villa near Pelican Beach, Waterslide, Bicycles, Kayaks...

1 Bedroom Bungalow 250m from beach (sleeps 4)

Pelican Nest,Cocoa Villa-6 acres on Grace Bay Beach-20% off...

Cozy Beach House 2 on Kite Boarding Beach.

Affordable Luxury Leeward near Pelican Beach, Grace Bay, Hot Tub...

Newly Renovated 8 Bedroom 7 Bath Villa Spectacular Views Ocean...

Brand New Waterfront Luxury Villa With Views!!

Large Waterfront Villa 3 King and 1 Twin Bedroom - Kayaks, SUPs...

Cozy Beach House on Kite Boarding Beach,W/Private Pool and kayak.

Beauty and the Beach!

10% OFF Until Dec 15!! 10 Steps to Grace Bay Beach, , 4BR...

Pelican Cottage - Minutes to Grace Bay Beach!!Bikes Incuded!!/Car...

'Barefoot Palms' Sept thru Nov 1, stay 9 pay for 7

SPECIAL OFFERS JUST ASK- CONCH VILLA GRACE BAY - Luxury Beach...

FREE CAR RENTAL - Luxury Ocean Front Villa on Grace Bay - ACCESS...

CONTACT US AT EXCEPTIONAL VILLAS FOR BEST OFFER Amazing Beach...

SPECIAL OFFERS JUST ASK- CONCH VILLA GRACE BAY - Luxury Beach...

CONTACT US DIRECTLY AT EXCEPTIONAL VILLAS FOR BEST OFFERAmazing...

Coral House - T&C