Summerland Key Vacation Rentals | Hotels



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Summerland Key Vacation Rentals and Hotels

HotStays.com features Summerland Key vacation rentals, Duck Key cabin rentals, Marathon Area cottage rentals, Key West holiday villas, Plantation Key bed and breakfast inns, Sugarloaf Key discount hotels and Tavernier condo rentals.
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Looking for Summerland Key hotels? View all hotels in the Summerland Key area.

We have over 100 properties in the Summerland Key, Florida area.
Please browse our top 30 properties below

Vacation Rentals in the Summerland Key/Marathon area. (22 miles away)

	Florida Keys Vacation Rentals– Atlantic Breezes #1682				From $850/week
	2-4 Beds	2.5 Baths	Sleeps 1-16	Condo
Private Waterfront setting with 50' Dock, Hot Tub, Sun Deck, Tiki Hut & Hammock- Marathon - Marathon, Florida Condo Rental 2 LARGE Luxury Waterfront condos (part of a 2 unit privately owned complex) conveniently located adjacent to each other on Sombrero Beach Road in the Florida Keys! You ...


	Fantastic 2BR/2BA Marathon condo - pets welcome #1160				From $995/week, $2,700/month
	2 Beds	2 Baths	Sleeps 2-6	Condo
Just minutes by boat to the Atlantic or Gulf, fantastic location! We have multiple units at this complex making it convenient for large families. This 2 bedroom, 2 full bathroom, ground floor unit in Marathon comes fully furnished & equipped. King bed in the Master, 2 twin beds in the Guest, Sleeper ...


	Condo in great vacation area near Coco Plum beach #1157				From $750/week, $2,100/month
	1 Beds	1.5 Baths	Sleeps 1-4	Condo
In a perfect location just minutes by boat to the Atlantic Ocean or Gulf! We have multiple units at this complex making it convenient for large families. This 1 bedroom, 1.5 bathrooms, ground floor unit is very clean and comes fully furnished & equipped. Screened Patio just steps from the boat ...


	Marathon vacation condo close to beach #1154				From $650/week, $1,695/month
	1 Beds	1 Baths	Sleeps 1-2	Condo
Marathon vacation condo completely tiled and fully equipped. Queen bed and full size sofa bed in living room sleeping 3-4 comfortably. Most pets are welcome upon approval. A pet friendly and secluded beach is only a short walk away. Includes a large boat slip, DVD player, cable TV, central AC, terrace ...


	Oceanfront home in Marathon w/ new furnishings #1151				From $2,600/month
	2 Beds	2 Baths	Sleeps 6	House
This is a newer two bedroom, two bathroom Marathon home on the oceanfront. Standing on stilts and overlooking the water, this home is perfect for your next vacation getaway. Our home includes 50 feet of dockage, a fenced in yard (perfect for kids & pets), three TVs, (32" flat screen in the living ...


	Florida keys Waterfront Home - Marathon #34				From $1,900/week
	2 Beds	1 Baths	Sleeps 6	House
Newly Built 2 Bedroom, fully equipped waterfront vacation home. sleeps 6 Ample deep water dockage in your back yard. Pool and sand beach access available. Our home was furnished in April, 2001 and includes sofa sleepers, linens, towels, dishes, television, VCR, cable, telephone, gas grill and more. Bedroom ...


	Fl Keys, 2 BR Home includes Private Island & Boat #32				From $2,295/week
	2 Beds	1 Baths	Sleeps 6	House
Our Florida Keys vacation rental combines the best of all worlds... a modern 2 bedroom shore house furnished with linens, towels and all the basic amenities. This rental also includes a quaint Bahamas cottage with an open air bunkhouse on our private tropical island!! Our 2 bedroom home is located ...

Vacation Rentals in the Summerland Key/Key West area. (29 miles away)

	Casa Manana Key West Cottage #1837				From $4,500/month
	2 Beds	2 Baths	Sleeps 6	Cottage
Casa Mañana at 800 Virginia Street is perfectly situated for the discriminating guest who wants to enjoy Key West at its finest. Located just two blocks from Duval Street, home of world famous watering holes, shopping and dining. Walking up Virginia Street brings you to White Street, the new Mecca ...


	Palm Isle- Key West #500				From $168/night
	1 Beds	1 Baths	Sleeps 4	Apartment
Welcome to Palm Isle – beauty and economy in Old Town Key West! Only one block west of Duval on Whitehead Street, and just doors down from the Hemingway House, this second story studio suite is equipped to make your stay in the islands comfortable and convenient. The house shares a lot with a giant ...


	Luxurious Penthouse - Key West #523				From $408/night
	4 Beds	4 Baths	Sleeps 1-12	Condo
Space, privacy, luxury - what more could you ask for, this penthouse has it all. Cathedral ceiling in the living room opening to a spacious balcony overlooking the harbor/marina. Gourmet kitchen with Corian counters is equipped down to the blender for those tropical concoctions for which Key West is ...


	Fully Equipped Key West Condo #518				From $178/night
	1-2 Beds	1-2 Baths	Sleeps 1-6	Condo
Our condos come with everything you could possibly need on a vacation. From the convenience of the dish washer and the washer/dryer to the relaxing heated pool you will find that your stay will be very peaceful and stress free. We have suites for two people and retreats for up to six people, so you ...


	Pleasant Waterfront Condo in Key West #516				From $178/night
	1-2 Beds	1-2 Baths	Sleeps 1-6	Condo
Welcome to Pelican Landing Resort on Garrison Bight Marina. Right in the heart of Key West, our resort includes a heated pool, private balconies and much more to accommodate you during your stay. This waterfront resort with dockage is within walking distance of world class charter fishing and diving, ...


	Lovely Condo on the Waterfront - Key West #515				From $178/night
	1-2 Beds	1-2 Baths	Sleeps 1-6	Condo
We offer suites (for 2 people) with one bedroom with a king bed; private bath; living room with queen sleeper sofa; dining area; fully equipped kitchen including microwave, blender, dishwasher, washer/dryer; breakfast bar seats four; living room and bedroom have sliding glass doors which open onto a ...


	Bonaire Retreat - Key West #514				From $198/night
	1-2 Beds	1-2 Baths	Sleeps 1-6	Condo
You will be located in Pelican Landing Resort on Garrison Bight Marina. This resort is within walking distance of world class charter fishing and diving, a short bicycle ride to the charm Old Town and right in the heart of Key West. This waterfront resort with dockage also includes a heated pool, private ...


	Pelican Landing Condo in Key West #513				From $178/night
	1-2 Beds	1-2 Baths	Sleeps 1-6	Condo
We offer a suite (for 2 people) featuring one bedroom with a king bed; private bath; living room with queen sleeper sofa; dining area; fully equipped kitchen including microwave, blender, dishwasher, washer/dryer; breakfast bar seats four; living room and bedroom have sliding glass doors which open onto ...


	The Seaport Suite - Key West #512				From $348/night
	4 Beds	2 Baths	Sleeps 8	House
Built in 1884 this large, historic building houses Re/Max Southernmost on the first floor. Seaport Suite, on the second floor, features four bedrooms and two baths – perfect for large families and groups. Furnished like the finest of captain's quarters, this expansive suite features original Dade County ...


	Toon Hall - Key West #511				From $348/night
	3 Beds	2 Baths	Sleeps 8	House
Enjoy comfort, lush tropical surroundings and unmatched privacy characterizing this former winter home of Pulitzer Prize winning cartoonist, author and artist, Jeff MacNelly. Designed to accommodate a large family or group, this three bedroom home has two full baths plus the quintessential Key West outdoor ...


	Island Oasis - Key West #510				From $408/night
	3 Beds	2 Baths	Sleeps 6	House
Foliage surrounds this modest Bohemian style house one block west of Duval Street. The painted Dade County Pine walls accent the antique furnishings from across the globe, including a carved headboard from Thailand and a handmade bed straight from the Costa Rican shores – topped off with local art and ...


	Havana Hideaway - Key West #509				From $398/night
	2 Beds	2.5 Baths	Sleeps 6	Cottage
This two story, two bedroom, two and a half bath home was built by Key West's premier architect/contractor and has been recently renovated and landscaped. One of the newest additions to the hideaway family, Havana Hideaway is the flagship cottage, representing privacy, luxury, location and convenience. ...


	Southern Cross - Key West #507				From $258/night
	2 Beds	2 Baths	Sleeps 6	Cottage
Sitting next to the lily pond with fountain or lounging in the shade of your own Royal Poinciana tree, Southern Cross is the perfect place to relax in paradise. This adorable one and a half story conch cottage, surrounded by exotic gardens, situated in the Tropical Village Compound, is the epitome of ...


	The Bahama House - Key West #506				From $258/night
	2 Beds	2 Baths	Sleeps 6	Cottage
This historic Bahamian-style Conch cottage is a prime example of turn-of-the-century island architecture. The modest two bedrooms, each with queen bed, two bath and queen sleeper-sofa is accented with Dade County pine walls, cathedral ceilings and island folk art, including original oil paintings, glass ...


	The Orchid Suite - Key West #502				From $178/night
	1 Beds	1 Baths	Sleeps 6	Apartment
This adorable suite is bi-level decorated in a rich contemporary Danish style. The bedroom is located upstairs with a bookcase divider which separates 2 different sleeping areas each with a queen bed covered with colorful Caribbean bedspreads completes the bedroom. The upstairs bath features a tiled ...


	Tropical Hideaway - Key West #501				From $198/night
	1 Beds	1 Baths	Sleeps 4	Apartment
Lush gardens surround this lovely restored two-story Bahamian house. This is a downstairs suite with one bedroom, full bath and features a living room with queen sleeper-sofa, cable TV, VCR, stereo with CD player, and a private telephone line with answering machine. The bedroom has a queen bed and cable ...


	Harbor view penthouse - Key West #522				From $338/night
	3 Beds	4 Baths	Sleeps 1-10	Condo
A bold Penthouse that says you have arrived! With a view of the harbor from your living room and a stunning balcony seat for Key West's world class sunsets from the upstairs two bedrooms......it just keeps getting better. This centrally air-conditioned three bedroom, four bathroom, two story suite ...


	Key West waterfront condo #519				From $178/night
	1-2 Beds	1-2 Baths	Sleeps 1-6	Condo
Our condos provide you with everything you could possibly need on a vacation. From the convenience of the dish washer and the washer/dryer to the relaxing heated pool you will find that your stay will be very peaceful and stress free. We have suites for two people and retreats for up to six people, ...


	Tropical Village Cottage - Key West #508				From $258/night
	2 Beds	2 Baths	Sleeps 5	Cottage
The Tropical Village Cottage is the epitome of modern Key West. This two bedroom, two bath conch cottage overlooks a shared oasis-style heated pool, sun deck and poolside grilling station. With all the amenities of contemporary living set in island style and décor, Tropical Village Cottage is your ticket ...


	The Tropical Retreat - Upstairs Suite in Key West #503				From $198/night
	2 Beds	1 Baths	Sleeps 4	Apartment
This cute upstairs suite has two bedrooms featuring queen beds. The fully equipped kitchen is perfect for the serious cook or enjoy your meals on the gas BBQ grill in a tropical setting. The living room that opens onto a private veranda, features cable TV, VCR, and stereo with CD player. One bath with ...


	Poolside Paradise - Key West #497				From $158/night
	1 Beds	1 Baths	Sleeps 2	Cottage
Poolside Paradise is one of our most popular properties, it features all the luxuries of high end vacation rentals – from a kitchen to cable TV and VCR, private telephone line with answering machine, shaded deck and poolside location – at an affordable nightly rate. Once the winter vacation suite of ...


	Well equipped waterfront Condo #520				From $178/night
	1-2 Beds	1-2 Baths	Sleeps 1-6	Condo
Our Suites (for 2 people) feature one bedroom with a king bed; private bath; living room with queen sleeper sofa; dining area; fully equipped kitchen including microwave, blender, dishwasher, washer/dryer; breakfast bar seats four; living room and bedroom have sliding glass doors which open onto a private ...


	Condo in Pelican Landing Resort - Key West #517				From $178/night
	1-2 Beds	1-2 Baths	Sleeps 1-6	Condo
Come stay at our beautiful waterfront condo. Whether you want a suite for two or a retreat for up to six guests you will surely enjoy your stay at Pelican Landing. We have nearby tennis, fishing, a heated pool and much more to keep you busy during your stay. Located in the heart of Key West, we are ...

We have over 100 properties in the Summerland Key, Florida area.
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Summerland Key Vacation Rentals | Hotels