Fleming Key Rentals
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Beautiful boat with wonderful deck anchored off of Fleming Key in Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
NOT IN A MARINA. Beautiful 31 foot Baha Cruiser boat anchored off Key West a couple miles from shore. The boat stays at ...
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From $695 per night (USD)VRBO
"LOST SHAKER OF SALT" ~ 3 Bed, 2 Bath Pet Friendly Home with 40' Private Pool
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
THE HEART OF OLD TOWN... Charming Old Town home in the heart of Key West. Located on Southard Street just steps from Du ...
From $695 per night (USD)VRBO
From $250 per night (USD)HomeAway
Charming Craftsman Home in Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Enjoy one of the most vibrant locations that Key West has to offer. The tropics meet historic craftsman charm at this ir ...
From $250 per night (USD)HomeAway
From $525 per night (USD)VRBO
"STARS" ~4 bedroom, 2 Bath Condo, Pool Heat, Downtown Location!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
When you do not need the entire compound but still want to enjoy this magnificent property in the heart of Old Town Key ...
From $525 per night (USD)VRBO
From $1295 per night (USD)HomeAway
"BOOMERANG BOATHOUSE" ~ Relax in This Beautiful 4 Bedroom/4 Bath Location!
- Bedrooms:
- 3.5
- Bathrooms:
- 4
- Sleeps:
- 8
RETURN TO EQUANIMITY... “Boomerang Boathouse” is nestled in the peaceful neighborhood locals refer to as The Meadows. T ...
From $1295 per night (USD)HomeAway
From $545 per night (USD)VRBO
"STRIPES" ~ Delightful Condo Located in the Heart of Old Town Key West!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
When you don't need the entire compound but still want to enjoy this magnificent property in the heart of Old Town Key ...
From $545 per night (USD)VRBO
From $745 per night (USD)HomeAway
"CAPT JACK'S HIDEAWAY" ~ Vintage Conch Cottage Located on a Quiet Lane!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
QUIET LOCATION, COMFORTABLE SPACE… Located in Old Town, this home sits on a quaint little lane. With limited homes on t ...
From $745 per night (USD)HomeAway
From $1095 per night (USD)VRBO
"SPARROW'S LANDING" ~ Casual Sophistication Located in a Quiet Neighborhood!
- Bedrooms:
- 4.5
- Bathrooms:
- 3
- Sleeps:
- 6
STEP INTO PARADISE... Located in the peaceful neighborhood locals call The Meadows, this home is set away from the noise ...
From $1095 per night (USD)VRBO
From $300 per night (USD)HomeAway
"BEACH HOUSE"~ Stunning 4B/4Ba Home with Private Pool in Truman Annex!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
PRESTIGIOUS TROPICAL RETREAT... Indulge in this spectacular two-story home situated in the premier gated community of hi ...
From $300 per night (USD)HomeAway
From $1445 per night (USD)VRBO
"BLUE ROOSTER" ~ Spectacular 4 Bed/4 Bath with Pool and Solarium in Old Town!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
OLD TOWN Paradise awaits in a quiet Old Town location. This four bedroom home is set on a cozy lane that is off the be ...
From $1445 per night (USD)VRBO
From $150 per night (USD)HomeAway
CONNIE'S COTTAGE - Old-world charm and elegant tropical living
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
28 Day minimum Rental: Old-world charm and elegant tropical living are waiting for you in this classic old town conch h ...
From $150 per night (USD)HomeAway
From $1145 per night (USD)VRBO
"SERENITY" ~ Relax in Ultimate Luxury and Comfort in Old Town Key West!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
LOCAL Spend time relaxing in Paradise in the perfect home. Serenity is a beautifully decorated, 3 bedroom home, with 3 ...
From $1145 per night (USD)VRBO
From $140 per night (USD)HomeAway
Quaint Old Town Key West Cottage with Heated Pool and Private Parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Conch Escape is a 2 bedroom 2 bath cottage situated in a private gated compound of ten homes in Old Town Key West. Thes ...
From $140 per night (USD)HomeAway
From $995 per night (USD)VRBO
"SEAHORSE COVE" ~ Tropical Luxury Located In The Heart Of Old Town Key West!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
FLAWLESS SETTING, PERFECT LOCATION… Tucked away on a hidden lane right in the middle of Old Town, this luxurious private ...
From $995 per night (USD)VRBO
From $59 per night (USD)HomeAway
The Galleon Resort Best Resort Location in KW
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This October condo is a 2BR, 2BA sunset/pool view sleeps 6. Condo has a full modern kitchen with granite/stainless, di ...
From $59 per night (USD)HomeAway
From $322 per night (USD)VRBO
**CASA SERENDIPITY @ OLD TOWN** Historic 3BR/2BA Home & Pool + LAST KEY SERVICE
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to yo ...
From $322 per night (USD)VRBO
From $117 per night (USD)HomeAway
30 night Minimum Stay Heart of Historic downtown 214 2 bed 2 1/2 Bath
- Bedrooms:
- 3.5
- Bathrooms:
- 2
- Sleeps:
- 4
This unit offers the perfect way to visit Key West, park your car and walk everywhere. Sunset celebration is only steps ...
From $117 per night (USD)HomeAway
From $150 per night (USD)VRBO
28 night minimum stay. 3 Bedroom House with a pool in Meadows
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Located on a quiet street in the Meadows of Key West; a tranquil residential neighborhood located just behind the Key We ...
From $150 per night (USD)VRBO
From $382 per night (USD)HomeAway
**THE SMILING IBIS @ OLD TOWN** Home & Pool Near Duval + LAST KEY SERVICES...
- Bedrooms:
- 4.5
- Bathrooms:
- 3
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to yo ...
From $382 per night (USD)HomeAway
From $205 per night (USD)VRBO
Heavenly Hideaway-Monthly 2BD/21/2BA Private Pool Home
- Bedrooms:
- 3.5
- Bathrooms:
- 3
- Sleeps:
- 6
HEAVENLY HIDEAWAY! We are complying with the directives listed on the Monroe County website. Please be aware that info ...
From $205 per night (USD)VRBO
From $215 per night (USD)HomeAway
37 ft. Economy Boat In Downtown Key West Sailboat Perfect Small Charter Boat
- Bedrooms:
- 2.5
- Bathrooms:
- 2
- Sleeps:
- 4
Hurry pick your spring break dates we are filling up fast in Key West! This is the REAL Key West Experience. Our mari ...
From $215 per night (USD)HomeAway
From $300 per night (USD)VRBO
2 bdrm Condo w/ boat slip Pelican Landing Flamingo
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Our beautiful waterfront condos have a range of room types to suite your every need. Whether you want a suite for two or ...
From $300 per night (USD)VRBO
From $500 per night (USD)HomeAway
Your Private Oasis in Old Town Key West - The Cigar Maker's Tropical Cottage!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Your tropical oasis in Historic Old Town Key West awaits for your monthly rental! 1890 Cigar Maker's Tropical Cottage re ...
From $500 per night (USD)HomeAway
From $273 per night (USD)VRBO
**PUERTA CORALINA @ OLD TOWN** Cottage Near Duval + LAST KEY SERVICE...
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to yo ...
From $273 per night (USD)VRBO
From $524 per night (USD)HomeAway
Luxury Waterfront home with elevator, private pool AND dock!
- Bedrooms:
- 4.5
- Bathrooms:
- 3
- Sleeps:
- 8
Traditional meets modern in an elegant way, right in the middle of one of Key West’s most historical districts. A stay a ...
From $524 per night (USD)HomeAway
From $393 per night (USD)VRBO
Luxury Waterfront at the Galleon Resort in Old Town
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
This condo is a 2BR/2BA Penthouse Loft on the 5th floor overlooking the marina. On the first floor is a full sized, ful ...
From $393 per night (USD)VRBO
From $90 per night (USD)HomeAway
Luxurious Historic House With Pool in Old Town 1 INTRODUCTORY RATES!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Monthly rental STUDIO with POOL just AVAILABLE. Same amenities. Save money if planing to come for over 14 days! Find it ...
From $90 per night (USD)HomeAway
From $50 per night (USD)VRBO
Rose Lane Villas - Villa Porta - 1 Bedroom - Downtown Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Nestled on a quiet lane in the heart of Old Town Key West, Rose Lane Villas is as close to the action as you'll get with ...
From $50 per night (USD)VRBO
From $240 per night (USD)HomeAway
Charming Home in Old Town
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Paradise on Pine, a monthly rental, is a picture perfect home that sits high above this lovely one way street with an i ...
From $240 per night (USD)HomeAway
From $174 per night (USD)VRBO
**HERE COMES THE SUN @ CASA MARINA** Home / Large Pool + LAST KEY SERVICES…
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to yo ...
From $174 per night (USD)VRBO
From $50 per night (USD)HomeAway
Rose Lane Villas - Villa Grande - 3 bedrooms - Downtown Key West
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Nestled on a quiet lane in the heart of Old Town Key West, Rose Lane Villas is as close to the action as you'll get with ...
From $50 per night (USD)HomeAway
From $500 per night (USD)VRBO
4 bd w/loft Condo w/ boat slip Pelican Landing St Croix
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
St. Croix Penthouse (for 12 people) features four bedrooms and four private baths. The master bedroom has a king bed, on ...
From $500 per night (USD)VRBO
From $132 per night (USD)HomeAway
Old Town Getaway
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Newly redecorated by a one of Key West top interior designers!! Elegant and adorable cottage on one of the nicest lanes ...
From $132 per night (USD)HomeAway
From $65 per night (USD)VRBO
The Hollinsed House "Victorian Delights" - Large 1 Bedroom
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Mingle with other guests around the tropical gardens surrounding the heated pool and sundeck creating the perfect settin ...
From $65 per night (USD)VRBO
From $209 per night (USD)HomeAway
PARADISE IN OLD TOWN!!!
- Bedrooms:
- 3.5
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to a beautiful house, hidden paradise, you never knew existed. Once you're entered into this hideaway, you'll ne ...
From $209 per night (USD)HomeAway
From $425 per night (USD)VRBO
Dreamworks Conch Cottage
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
PEACEFUL RETREAT... A quintessential Key West cottage in the heart of Old Town and only a few blocks away from Higgs Bea ...
From $425 per night (USD)VRBO
From $100 per night (USD)HomeAway
Studio overlooking historic Key West waterfront.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Overlooking the Historic Key West Bight, this bright and clean studio features a fully equipped kitchen, renovated bathr ...
From $100 per night (USD)HomeAway
From $2059 per night (USD)VRBO
Seaport Treasure Estate
- Bedrooms:
- 7.5
- Bathrooms:
- 6
- Sleeps:
- 12
An exceptional degree of creativity is displayed in this detailed renovation that artfully intertwines 3 dwellings: two ...
From $2059 per night (USD)VRBO
From $180 per night (USD)HomeAway
COLONY CALYPSO - A quaint 1 Bedroom Cottage just two blocks to Duval
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Part of a small collection of cottages known as The Colony, this quaint cottage sits to the back of the property and is ...
From $180 per night (USD)HomeAway
From $449 per night (USD)VRBO
Down Island Digs ~ Downtown with Private Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Everything about this historic Key West tropical gem adds up to make a precious private garden cottage. Sitting in the m ...
From $449 per night (USD)VRBO
From $325 per night (USD)HomeAway
200 feet from Duval Street, but quiet and secluded
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Key West Villas is a small, historic property located 200 feet from Duval Street. This is gorgeous two bedroom, two bat ...
From $325 per night (USD)HomeAway
From $409 per night (USD)VRBO
30% OFF 2021 28 nts PRKING FREE Ft Zach BCH PASS/ COMM POOL
- Bedrooms:
- 3.5
- Bathrooms:
- 3
- Sleeps:
- 6
I will send you a special offer with the additional discount -30% OFF any month in 2021....Old Town -Whitehead St- BEST ...
From $409 per night (USD)VRBO
From $100 per night (USD)HomeAway
Beautifully restored 2 bed apartment in historic Old Town neighborhood.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Located on one of the best streets in Old Town you are just three blocks from the Harbor….home to the freshest seafood r ...
From $100 per night (USD)HomeAway
From $240 per night (USD)VRBO
~ THE STEAMPLANT 210 ~ Luxurious Condo w/ Breathtaking Views & Rooftop Pool
- Bedrooms:
- 4.5
- Bathrooms:
- 3
- Sleeps:
- 8
THE PROPERTY: Welcome to Steamplant 210! Two Level, 5 Star Luxury Residence with breathtaking panoramic views of Key Wes ...
From $240 per night (USD)VRBO
From $148 per night (USD)HomeAway
~ CASABLANCA ~ Fabulous Cottage w/ HEATED Pool, Parking & Tons of Sun!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
THE PROPERTY: Casablanca is the perfect Key West vacation rental for those seeking a good time, but who would like to st ...
From $148 per night (USD)HomeAway
From $110 per night (USD)VRBO
Turn lemons into lemonade Jan. Feb. & March. Prices lowest ever!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
STERILIZED WITH 4 QUAD CLEANING SYSTEM ...
From $110 per night (USD)VRBO
From $260 per night (USD)HomeAway
~TROPICAL DREAM~ World Class Luxury Home w/Pool, Roma Spa & Parking. Dogs OK!
- Bedrooms:
- 4.5
- Bathrooms:
- 4
- Sleeps:
- 8
THE PROPERTY: We guarantee that Tropical Dream will fulfill even the highest expectations. Amazing LUXURY Vacation Home ...
From $260 per night (USD)HomeAway
From $940 per night (USD)VRBO
~ VILLA JOSINE ~ Luxurious "Old Town" Home w/ 18'Heated Pool & Parking!
- Bedrooms:
- 5.5
- Bathrooms:
- 4
- Sleeps:
- 8
THE PROPERTY: Villa Josine is an amazingly beautiful home located in one of the most sought after locations in Key West ...
From $940 per night (USD)VRBO
From $240 per night (USD)HomeAway
~STEAMPLANT 207~ Luxury 3-Story Condo w/ Pvt Rooftop Pool & Amazing Views!
- Bedrooms:
- 4.5
- Bathrooms:
- 3
- Sleeps:
- 8
THE PROPERTY: Steamplant 207! Two Level, 5 Star Luxury Residence Breathtaking panoramic views of Key West. * Private Ro ...
From $240 per night (USD)HomeAway
From $450 per night (USD)VRBO
The Caroline House Estate
- Bedrooms:
- 4.5
- Bathrooms:
- 5
- Sleeps:
- 10
This gorgeous classical Key West Estate property is quite possibly the most stylish blend of historic Victorian-Caribbea ...
From $450 per night (USD)VRBO
From $329 per night (USD)HomeAway
Secret Villa I @ Old Town with Private Pool, close to Duval!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
- Secret Villa I - A Newly Renovated, Private Sanctuary, Centrally Located off of Duval Street with your very own priv ...
From $329 per night (USD)HomeAway
From $130 per night (USD)VRBO
Namaste 'the spirit within me salutes the spirit within you'
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 2
Tucked away in an inviting compound you'll find a blissful retreat called Namaste; a tranquil and relaxing one bedroom B ...
From $130 per night (USD)VRBO
From $485 per night (USD)HomeAway
~ SOUTHARD COMFORT ~ Historic Home w/ Heated Pool, Parking & Quiet Location!
- Bedrooms:
- 3.5
- Bathrooms:
- 3
- Sleeps:
- 6
THE PROPERTY: “Southard Comfort” is true Island living in Historic "Old Town" Key West. Nancy & Carl welcome you to the ...
From $485 per night (USD)HomeAway
From $325 per night (USD)VRBO
Downtown Cottage in Historic District-No Contact Check-In
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Stay in the Conch Republic Consul General's Cottage. Historic Cottage Atocha offers 2 bedrooms, living room with orginia ...
From $325 per night (USD)VRBO
From $130 per night (USD)HomeAway
"Tranquility " at Ann Street Gardens Steps from Duval
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Location is ideal for this wonderful one bedroom retreat. A lush, inviting compound created so owners and guests could e ...
From $130 per night (USD)HomeAway
From $329 per night (USD)VRBO
Secret Villa II @ Old Town: with Private Pool, close to Duval!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
- Secret Villa II - A Newly Renovated, Private Sanctuary, Centrally Located off of Duval Street with your very own pri ...
From $329 per night (USD)VRBO
From $200 per night (USD)HomeAway
Ann Street Cottage: A bright and airy home near Duval Street
- Bedrooms:
- 2.5
- Bathrooms:
- 1
- Sleeps:
- 2
Tucked away in an inviting compound you'll find the perfect hideaway called Ann Street Cottage; a charming one bedroom c ...
From $200 per night (USD)HomeAway
From $214 per night (USD)VRBO
Elizabeth Retreat: A three bedroom historic home in Old Town
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
28 DAY MINIMUM RENTAL Walk the historic streets of Key West, live in Old Town in a quiet residential neighborhood. Just ...
From $214 per night (USD)VRBO
From $325 per night (USD)HomeAway
Downtown Cottage just off famous Duval Street-No Contact Check-In
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Stay in the Conch Republic Consul General's Cottage. Historic Carriage House is located a few blocks from famous Duval S ...
From $325 per night (USD)HomeAway
From $90 per night (USD)VRBO
Luxurious Historic House With Pool in Old Town INTRODUCTORY RATES!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Monthly rental STUDIO with POOL just AVAILABLE. Same amenities. Save money if planing to come for over 14 days! Find it ...
From $90 per night (USD)VRBO
From $414 per night (USD)HomeAway
Key West Oasis, Seperate Cottage, Very Private Pool & Back Yard
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Please Note: Key West Oasis is NOT suitable for families with young children, as the 2nd bedroom is not attached to the ...
From $414 per night (USD)HomeAway
From $450 per night (USD)VRBO
Historic House, Gorgeous Porch, Great Location, See 5 Star Reviews
- Bedrooms:
- 4.5
- Bathrooms:
- 4
- Sleeps:
- 8
Treat yourself, your family and friends to a grand Key West home ideal for an extended stay on the island. This wonderfu ...
From $450 per night (USD)VRBO
From $180 per night (USD)HomeAway
~LEMONADE MERMAID~ Dog-Friendly, Heated POOL, Fenced Yard. Off street parking
- Bedrooms:
- 3.5
- Bathrooms:
- 2
- Sleeps:
- 5
THE PROPERTY: You’re going to delight being in Lemonade Mermaid! This adorable gingerbread cottage with amazing front p ...
From $180 per night (USD)HomeAway
From $100 per night (USD)VRBO
Peaceful One Bedroom Retreat Located Blocks From Duval Street And The Harbor.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This one bedroom loft apartment with full kitchen and laundry has everything you need for an extended stay! Located on o ...
From $100 per night (USD)VRBO
From $527 per night (USD)HomeAway
**SOUTHERNMOST BLISS @ OLD TOWN** Lavish Home & Pool + LAST KEY SERVICES...
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to yo ...
From $527 per night (USD)HomeAway
From $872 per night (USD)VRBO
**STAR OF THE SEAPORT @ OLD TOWN** Huge Home & Pool + LAST KEY SERVICES...
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 12
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to yo ...
From $872 per night (USD)VRBO
From $124 per night (USD)HomeAway
**LA CASITA EN CIMA @ OLD TOWN** Quaint Cottage By Duval + LAST KEY SERVICE...
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to yo ...
From $124 per night (USD)HomeAway
From $300 per night (USD)VRBO
2 bdrm Condo w/ boat slip Pelican Landing Eleuthera
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Our beautiful waterfront condos have a range of room types to suite your every need. Whether you want a suite for two or ...
From $300 per night (USD)VRBO
From $872 per night (USD)HomeAway
**THE LIME & THE COCONUT @ OLD TOWN** 6BR/6BA Compound + LAST KEY SERVICES..
- Bedrooms:
- 9
- Bathrooms:
- 6
- Sleeps:
- 16
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to yo ...
From $872 per night (USD)HomeAway
From $472 per night (USD)VRBO
**HEAVENLY ZEN @ THE SEAPORT** Lavish Home & Pool + LAST KEY SERVICES...
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to yo ...
From $472 per night (USD)VRBO
From $99 per night (USD)HomeAway
2-Story Waterfront Condo near Old Town + Pool and Boat Slip, Available Monthly
- Bedrooms:
- 3.5
- Bathrooms:
- 2
- Sleeps:
- 6
Bay Villas is a charming 2-story waterfront condo located on Hilton Haven Road, a quiet cul-de-sac on Trumbo Point, whic ...
From $99 per night (USD)HomeAway
From $506 per night (USD)VRBO
PAGITT HOUSE - Old Town Weekly Rental - Private Pool - 3BR/2BA - Sleeps 6
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
WELCOME TO PAGITT HOUSE! We are complying with the directives listed on the Monroe County website. Please be aware ...
From $506 per night (USD)VRBO
From $59 per night (USD)HomeAway
Lock-Out Unit at the Galleon Resort - Best Resort Location In KW
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Studio(lock-out) for rent 5th floor. The Galleon Resort has its own marina, fishing charters on-site, tiki bar that serv ...
From $59 per night (USD)HomeAway
From $50 per night (USD)VRBO
Rose Lane Villas - Villa Aqua - 2 King Bedrooms - Downtown Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Nestled on a quiet lane in the heart of Old Town Key West, Rose Lane Villas is as close to the action as you'll get with ...
From $50 per night (USD)VRBO
From $234 per night (USD)HomeAway
Key West Suites Hotel #201 on Duval
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 6
Key West Suites Hotel #201 Welcome to your charming private studio apartment right on Duval street! Built in 1919, it u ...
From $234 per night (USD)HomeAway
From $350 per night (USD)VRBO
Galleon Resort Waterfront Luxury in Old Town Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 5
This is a large (1245 SF) 1BR/1BA condo on the 6th floor of the Galleon Resort & Marina.....and is a one of a kind. It ...
From $350 per night (USD)VRBO
From $343 per night (USD)HomeAway
**VILLA OLIVIETTA @ SOLARES HILL** Upscale Home & Pool + LAST KEY SERVICES...
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to yo ...
From $343 per night (USD)HomeAway
From $125 per night (USD)VRBO
"CAROLINE ON MY MIND" ~ Comfortable, Modern Condo Two Blocks from Duval!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
CLASSIC KEY This retreat is an elegant two bedroom, 2 bath condominium one block off of famous Duval Street. Second flo ...
From $125 per night (USD)VRBO
From $382 per night (USD)HomeAway
**THE CONTENTED CRANE @ OLD TOWN** Home & Pool Near Duval + LAST KEY SERVICES...
- Bedrooms:
- 4.5
- Bathrooms:
- 3
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to yo ...
From $382 per night (USD)HomeAway
From $478 per night (USD)VRBO
PINEAPPLE COTTAGE: 2BR/2BA-Pvt Pool -1/2 block to Duval
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
WELCOME TO PINEAPPLE COTTAGE! We are complying with the directives listed on the Monroe County website. Please be awa ...
From $478 per night (USD)VRBO
From $763 per night (USD)HomeAway
**THE IBIS & THE CRANE @ OLD TOWN** Compound Near Duval + LAST KEY SERVICES...
- Bedrooms:
- 9
- Bathrooms:
- 6
- Sleeps:
- 16
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to yo ...
From $763 per night (USD)HomeAway
From $584 per night (USD)VRBO
**THE ARTISTS' MUSE @ LOVE LANE** Immaculate Home & Pool + LAST KEY SERVICES...
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to yo ...
From $584 per night (USD)VRBO
From $900 per night (USD)HomeAway
Admirals Treasure in the Annex
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
When you are seeking one of the best large home accommodations, look no have found Admirals Treasure, a fabulous 4 bedr ...
From $900 per night (USD)HomeAway
From $329 per night (USD)VRBO
Absolute Key West in the Truman Annex
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This Private home is located in the historic Truman Annex of old town Key West, where you can get away from it all while ...
From $329 per night (USD)VRBO
From $436 per night (USD)HomeAway
**THE ZESTY LIME @ OLD TOWN** Beautifully Restored Home + LAST KEY SERVICES…
- Bedrooms:
- 4.5
- Bathrooms:
- 3
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to yo ...
From $436 per night (USD)HomeAway
From $50 per night (USD)VRBO
Rose Lane Villas - Villa Alta - 1 bedroom - Sleeps 4 - Downtown Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Nestled on a quiet lane in the heart of Old Town Key West, Rose Lane Villas is as close to the action as you'll get wit ...
From $50 per night (USD)VRBO
From $480 per night (USD)HomeAway
SEAPORT SUNSETS at Galleon Resort in Old Town (Beach-Pool-BBQ)
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
GALLEON RESORT LUXURY OCEANFRONT CONDO RENTAL 45 FT FROM THE WATER WITH BREATHTAKING VIEWS OF KEY WEST HARBOR, SUNSET KE ...
From $480 per night (USD)HomeAway
From $749 per night (USD)VRBO
Oversized Oldtown home for the whole family with private pool and dock!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
"Captain's Daughter” is a spacious home with the ability to sleep a large group comfortably, a private pool and tropical ...
From $749 per night (USD)VRBO
From $389 per night (USD)HomeAway
**CASA FELIZ @ OLD TOWN** Historic Home & Pool | Near Duval + LAST KEY SERVICES.
- Bedrooms:
- 5
- Bathrooms:
- 3
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to yo ...
From $389 per night (USD)HomeAway
From $409 per night (USD)VRBO
**DARLING OF DUVAL @ OLD TOWN** Estate Cottage + Spa + LAST KEY SERVICES…
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to yo ...
From $409 per night (USD)VRBO
From $683 per night (USD)HomeAway
**MAISON TROPICALE @ OLD TOWN** Historic Home + LAST KEY SERVICES...
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to yo ...
From $683 per night (USD)HomeAway
From $491 per night (USD)VRBO
**GOOD VIBRATIONS @ OLD TOWN** Unique Villa & Pool + LAST KEY SERVICES…
- Bedrooms:
- 5.5
- Bathrooms:
- 4
- Sleeps:
- 10
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to yo ...
From $491 per night (USD)VRBO
From $204 per night (USD)HomeAway
**HAVANA HOUSE @ OLD TOWN** Elegant Cottage Near Duval + LAST KEY SERVICES...
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to yo ...
From $204 per night (USD)HomeAway
From $300 per night (USD)VRBO
2 bdrm Condo w/ boat slip Pelican Landing Aruba
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Our beautiful waterfront condos have a range of room types to suite your every need. Whether you want a suite for two or ...
From $300 per night (USD)VRBO
From $50 per night (USD)HomeAway
Rose Lane Villas - Villa Vista - 2 bedrooms - Downtown Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Nestled on a quiet lane in the heart of Old Town Key West, Rose Lane Villas is as close to the action as you'll get with ...
From $50 per night (USD)HomeAway
From $300 per night (USD)VRBO
2 bdrm Condo w/ boat slip Pelican Landing Bonaire
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Our beautiful waterfront condos have a range of room types to suite your every need. Whether you want a suite for two or ...
From $300 per night (USD)VRBO
From $218 per night (USD)HomeAway
**SOUTHERN STAR @ THE MEADOWS** 4BR Home & Pool + LAST KEY SERVICES…
- Bedrooms:
- 4.5
- Bathrooms:
- 4
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to yo ...
From $218 per night (USD)HomeAway
From $300 per night (USD)VRBO
2 bdrm Condo w/ boat slip Pelican Landing Andros
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Our beautiful waterfront condos have a range of room types to suite your every need. Whether you want a suite for two or ...
From $300 per night (USD)VRBO
From $487 per night (USD)HomeAway
**CASA OLIVIANA @ SOLARES HILL** Grand Home & Pool + LAST KEY SERVICES...
- Bedrooms:
- 7
- Bathrooms:
- 6
- Sleeps:
- 12
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to yo ...
From $487 per night (USD)HomeAway
From $189 per night (USD)VRBO
**HEART of the HARBOR @ THE SEAPORT** Old Town Living & Pool + LAST KEY SERVICES
- Bedrooms:
- 4.5
- Bathrooms:
- 3
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to yo ...
From $189 per night (USD)VRBO
From $436 per night (USD)HomeAway
**THE TOASTED COCONUT @ OLD TOWN** Fully Restored + Pool + LAST KEY SERVICES…
- Bedrooms:
- 4.5
- Bathrooms:
- 3
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to yo ...
From $436 per night (USD)HomeAway
From $545 per night (USD)VRBO
**AMERICANA TROPICALE @ OLD TOWN** Home & Pool by Duval + LAST KEY SERVICES...
- Bedrooms:
- 5.5
- Bathrooms:
- 4
- Sleeps:
- 10
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to yo ...
From $545 per night (USD)VRBO
From $531 per night (USD)HomeAway
**THE ADMIRAL'S ESTATE** Grand Home & Pool + LAST KEY SERVICES...
- Bedrooms:
- 6.5
- Bathrooms:
- 5
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to yo ...
From $531 per night (USD)HomeAway
From $550 per night (USD)VRBO
**COASTAL CABANA @ LOVE LANE** Cul-de-Sac Home & Pool + LAST KEY SERVICES...
- Bedrooms:
- 3.5
- Bathrooms:
- 3
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to yo ...
From $550 per night (USD)VRBO
From $159 per night (USD)HomeAway
~ MY HAPPY PLACE ~ Tropical Home w/ Private Pool In Heart of 'Old Town' KW
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
THE PROPERTY: My Happy Place is an exemplary renovation of an historic, Key West house. It retains its original charact ...
From $159 per night (USD)HomeAway
From $380 per night (USD)VRBO
Havana Lane: An updated classic conch cottage with still a rustic edge!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This charming conch cottage has gone through some wonderful changes in 2019! Enter the private courtyard of the home, t ...
From $380 per night (USD)VRBO
From $150 per night (USD)HomeAway
Albury Bungalow: A quiet retreat in the Meadows
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
28 DAY MINIMUM RENTAL A perfect spot for two couples, two singles or others wanting privacy as well as togetherness. Th ...
From $150 per night (USD)HomeAway
From $59 per night (USD)VRBO
Beautiful views and close to Duval Street festivities and boat docks. Wks 29-30.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Two bedroom condo units in the premier Galleon Resort with unique access to dockage and rental boats. The units include ...
From $59 per night (USD)VRBO
From $365 per night (USD)HomeAway
Downtown Location in Historic District-No Contact Check-In
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Stay in the Conch Republic Consul General's Cottage. This one bedroom cottage is located in the historic district and o ...
From $365 per night (USD)HomeAway
From $185 per night (USD)VRBO
The Hollinsed House - Harvey's Haven - Great Location!!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to Harvey's Haven - beauty and economy in the heart of Old Town Key West! Ideally located at 611 Southard Street ...
From $185 per night (USD)VRBO
From $182 per night (USD)HomeAway
THOMPSON'S COURT - Mid Town Getaway with pool & jacuzzi
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
28 DAY MINIMUM RENTAL Thompson's Court is the quintessential south Florida home: a sprawling, peach-colored, ranch-styl ...
From $182 per night (USD)HomeAway
From $125 per night (USD)VRBO
Key West Coop - our tropical oasis in the Historic District close to everything
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Beautifully remodeled Cottage in the Historic District of Key West. Walk or ride your bike to anywhere on the island. ...
From $125 per night (USD)VRBO
From $240 per night (USD)HomeAway
~ STEAMPLANT 208 ~ Luxurious Condo w/ Breathtaking Views & Rooftop Pool
- Bedrooms:
- 4.5
- Bathrooms:
- 3
- Sleeps:
- 8
THE PROPERTY: Welcome to Steamplant 208! Two Level, 5 Star Luxury Residence with breathtaking panoramic views of Key Wes ...
From $240 per night (USD)HomeAway
From $142 per night (USD)VRBO
~ SOLARIS GARDEN ~ Enjoy Old Town Livin' Just A Short Walk to All the Action!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
THE PROPERTY: Solaris Garden, located on one of Key West’s most private slow lanes, is a Bohemian dream! This one-bedroo ...
From $142 per night (USD)VRBO
From $260 per night (USD)HomeAway
Hidden Treasure-Pet-friendly, Close to Duval St., Outdoor Deck, Shared Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Hidden from sight, among a colony of freestanding conch cottages, surrounded by lush tropical landscaping, you will find ...
From $260 per night (USD)HomeAway
From $375 per night (USD)VRBO
Mango Cottage- 2BR/2BA Family-Friendly Old Town Private Home with Private Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Mango Cottage This recently-restored historic Conch house is an excellent vacation home. The kitchen and bathrooms have ...
From $375 per night (USD)VRBO
From $35 per night (USD)HomeAway
Galleon Resort - Balcony Overlooking Marina w/ Stair to Boardwalk, Sleeps 6
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
WATERFRONT, TWO BEDROOM, 2 BATH, FULL KITCHEN IN KEY WEST HISTORIC SEAPORT Condo type unit with an area of 1300 square ...
From $35 per night (USD)HomeAway
From $571 per night (USD)VRBO
*** PRICE REDUCTION *** Penthouse Suite KW Galleon Resort, Avail 7/6-7/10/2021
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
The Galleon Resort is the best location in Key West. We own week 26 and 27, so for 2021, that is from Saturday, June 26 ...
From $571 per night (USD)VRBO
From $275 per night (USD)HomeAway
A spacious "Penthouse" condo at The Banyan
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Just steps from Duval Street, this secluded resort appears off the beaten path, yet is truly situated a stone's throw fr ...
From $275 per night (USD)HomeAway
From $600 per night (USD)VRBO
Flirty Flamingo Key West
- Bedrooms:
- 5
- Bathrooms:
- 3
- Sleeps:
- 8
Flirty Flamingo is luxurious and in a prime Key West location. Built in 1998 and meticulously cared for this spacious 3 ...
From $600 per night (USD)VRBO
From $118 per night (USD)HomeAway
SUITE CAROLINE - Luxury condo within steps to Key West's historic seaport
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
28 DAY MINIMUM RENTAL Situated in the heart of Old Town Key West, on the legendary Caroline Street, this beautifully res ...
From $118 per night (USD)HomeAway
From $874 per night (USD)VRBO
Architects Cottage in fantastic Old Town location!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
We have a wonderful MONTHLY rental to offer you: an historic 'conch' house has been completely redesigned and custom cra ...
From $874 per night (USD)VRBO
From $190 per night (USD)HomeAway
~CASA KEY WEST~ Historical Home w/ Plunge Pool In PERFECT Location.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
THE PROPERTY: As seen on HGTV's television series "ISLAND LIFE"! One of the Grand Dames of Key West, this two-story fa ...
From $190 per night (USD)HomeAway
From $225 per night (USD)VRBO
Ashe Splashe: A beautiful restoration of a historic Key West property
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
28 DAY MINIMUM RENTAL From the owners of South of Frances, here is another beautiful, historic restoration project. Th ...
From $225 per night (USD)VRBO
From $175 per night (USD)HomeAway
TRANQUILITY - Quaint Cottage in Gated Compound with Shared Pool + Private BBQ
- Bedrooms:
- 2.5
- Bathrooms:
- 1
- Sleeps:
- 4
Settled in a small community of Old Town yet only a short walk to Duval Street, this lovely cottage offers everything yo ...
From $175 per night (USD)HomeAway
From $158 per night (USD)VRBO
~ POINCIANA TREETOP ~ Updated Suite w/ Private Parking In Great Location!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
THE PROPERTY: Welcome to Poinciana Treetop, a sunny one-bedroom Key West vacation rental. The casual upstairs unit is lo ...
From $158 per night (USD)VRBO
From $103 per night (USD)HomeAway
Great location! Everything one would need. 3 month minimum
- Bedrooms:
- 2.5
- Bathrooms:
- 2
- Sleeps:
- 4
This quiet, lovely tropical cottage has lots of privacy where guests enjoy a small pond with a waterfall as well as a ga ...
From $103 per night (USD)HomeAway
From $559 per night (USD)VRBO
Historic Seaport Luxury Home -1 Block to Duval St & Seaport Marina
- Bedrooms:
- 4.5
- Bathrooms:
- 4
- Sleeps:
- 8
Location, Location, Location! This quintessential Key West Historic home is 4 bedroom 3.5 bathroom house is located ju ...
From $559 per night (USD)VRBO
From $375 per night (USD)HomeAway
Fleming-O Quiet Retreat in the Heart of Old Town Key West
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Fleming-O (pronounced “Flamingo”) is located on one-way Fleming Street, only two blocks from world famous Duval Street a ...
From $375 per night (USD)HomeAway
From $240 per night (USD)VRBO
Old Town Harborside Luxury Key West Condo: Private Pool, Garage
- Bedrooms:
- 4.5
- Bathrooms:
- 3
- Sleeps:
- 8
THE PROPERTY: Welcome to Steamplant 212! Two Level, 5 Star Luxury Residence with breathtaking panoramic views of Key Wes ...
From $240 per night (USD)VRBO
From $240 per night (USD)HomeAway
~ Steamplant 209 ~ Luxurious Condo w/ Breathtaking Views & Rooftop Pool
- Bedrooms:
- 4.5
- Bathrooms:
- 3
- Sleeps:
- 8
THE PROPERTY: Welcome to Steamplant 209! Two Level, 5 Star Luxury Residence with breathtaking panoramic views of Key Wes ...
From $240 per night (USD)HomeAway
From $500 per night (USD)VRBO
Ohana Paradise At The Historic Seaport , Old Town. Private Home.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Experience what is like to live in Old Town at the desirable Historic Seaport. This beautiful home is filled with amaz ...
From $500 per night (USD)VRBO