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Check prices for these dates
Top last-minute deals in Summerland Key
$139 nightly
The price is $313
$313 total
Oct 20 - Oct 22
Total with taxes and fees
$228 nightly
The price is $513
$513 total
Oct 20 - Oct 22
Total with taxes and fees




Sugarloaf Key RV Resort & Cottages
Sugarloaf Key RV Resort & CottagesSummerland Key
9.2 out of 10, Wonderful, (35)
9.2/10
Wonderful
(35)
$170 nightly
The price is $382
$382 total
Oct 20 - Oct 22
Total with taxes and fees
$189 nightly
The price is $426
$426 total
Oct 20 - Oct 22
Total with taxes and fees




Sugarloaf Key Hotel at KOA Resort
Sugarloaf Key Hotel at KOA ResortSummerland Key
9.8 out of 10, Exceptional, (649)
9.8/10
Exceptional
(649)
$204 nightly
The price is $460
$460 total
Oct 20 - Oct 22
Total with taxes and fees




Atlantic View Luxury Villa with Pool
Atlantic View Luxury Villa with PoolSummerland Key
7.4 out of 10, Good, (3)
7.4/10
Good
(3)
$750 nightly
The price is $1,688
$1,688 total
Oct 20 - Oct 22
Total with taxes and fees
Check out pet-friendly hotels in Summerland Key




9.0 out of 10, Wonderful, (1001)
9.0/10
Wonderful
(1001)
$184 nightly
The price is $207
$207 total
Nov 18 - Nov 19
Total with taxes and fees




7.8 out of 10, Good, (1000)
7.8/10
Good
(1000)
$140 nightly
The price is $158
$158 total
Oct 26 - Oct 27
Total with taxes and fees




Affordable Dog Friendly Keys Retreat in Venture Out Near Key West
Affordable Dog Friendly Keys Retreat in Venture Out Near Key WestCudjoe Key
10.0 out of 10, Exceptional, (1)
10/10
Exceptional
(1)
$376 nightly
The price is $417
$417 total
Oct 27 - Oct 28
Total with taxes and fees




Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated AccessCudjoe Key
10.0 out of 10, Exceptional, (1)
10/10
Exceptional
(1)
$415 nightly
The price is $460
$460 total
Nov 2 - Nov 3
Total with taxes and fees




Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West
Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key WestCudjoe Key
8.6 out of 10, Excellent, (4)
8.6/10
Excellent
(4)
$427 nightly
The price is $475
$475 total
Oct 20 - Oct 21
Total with taxes and fees




Canal Front Retreat w/ Ocean Views, 35' Dock & Golf Cart Option
Canal Front Retreat w/ Ocean Views, 35' Dock & Golf Cart OptionCudjoe Key
9.4 out of 10, Exceptional, (18)
9.4/10
Exceptional
(18)
$460 nightly
The price is $510
$510 total
Oct 21 - Oct 22
Total with taxes and fees




Seabreeze Escape WF RV Lot 489
Seabreeze Escape WF RV Lot 489Cudjoe Key
8.0 out of 10, Very good, (1)
8.0/10
Very good
(1)
$243 nightly
The price is $261
$261 total
Oct 19 - Oct 20
Total with taxes and fees




Canal-Front Retreat with Dock, Pool & Open Ocean Views
Canal-Front Retreat with Dock, Pool & Open Ocean ViewsCudjoe Key
9.0 out of 10, Wonderful, (13)
9.0/10
Wonderful
(13)
$460 nightly
The price is $510
$510 total
Oct 22 - Oct 23
Total with taxes and fees




Kelly's Kabin - Adorable Private Summerland Key Cottage
Kelly's Kabin - Adorable Private Summerland Key CottageSummerland Key
9.8 out of 10, Exceptional, (129)
9.8/10
Exceptional
(129)
$443 nightly
The price is $493
$493 total
Oct 19 - Oct 20
Total with taxes and fees




Little Piece of Paradise #233 Waterfront Cottage with Dock, Pool & Canal Views
Little Piece of Paradise #233 Waterfront Cottage with Dock, Pool & Canal ViewsCudjoe Key
9.0 out of 10, Wonderful, (2)
9.0/10
Wonderful
(2)
$439 nightly
The price is $487
$487 total
Oct 19 - Oct 20
Total with taxes and fees
Hotels with a pool in Summerland Key you'll enjoy




9.0 out of 10, Wonderful, (1001)
9.0/10
Wonderful
(1001)
$184 nightly
The price is $207
$207 total
Nov 18 - Nov 19
Total with taxes and fees




8.2 out of 10, Very good, (1001)
8.2/10
Very good
(1001)
$119 nightly
The price is $134
$134 total
Oct 26 - Oct 27
Total with taxes and fees




7.8 out of 10, Good, (1000)
7.8/10
Good
(1000)
$140 nightly
The price is $158
$158 total
Oct 26 - Oct 27
Total with taxes and fees




SAVE BIG $$$ OCT./NOV. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
SAVE BIG $$$ OCT./NOV. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDSCudjoe Key
9.6 out of 10, Exceptional, (98)
9.6/10
Exceptional
(98)
$391 nightly
The price is $434
$434 total
Oct 21 - Oct 22
Total with taxes and fees




Affordable Dog Friendly Keys Retreat in Venture Out Near Key West
Affordable Dog Friendly Keys Retreat in Venture Out Near Key WestCudjoe Key
10.0 out of 10, Exceptional, (1)
10/10
Exceptional
(1)
$376 nightly
The price is $417
$417 total
Oct 27 - Oct 28
Total with taxes and fees




Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated AccessCudjoe Key
10.0 out of 10, Exceptional, (1)
10/10
Exceptional
(1)
$415 nightly
The price is $460
$460 total
Nov 2 - Nov 3
Total with taxes and fees




SAVE BIG $$$ OCT./NOV. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
SAVE BIG $$$ OCT./NOV. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDSCudjoe Key
9.4 out of 10, Exceptional, (113)
9.4/10
Exceptional
(113)
$400 nightly
The price is $444
$444 total
Oct 19 - Oct 20
Total with taxes and fees




Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West
Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key WestCudjoe Key
8.6 out of 10, Excellent, (4)
8.6/10
Excellent
(4)
$427 nightly
The price is $475
$475 total
Oct 20 - Oct 21
Total with taxes and fees




Canal-Front Retreat with Dock, Pool & Open Ocean Views
Canal-Front Retreat with Dock, Pool & Open Ocean ViewsCudjoe Key
9.0 out of 10, Wonderful, (13)
9.0/10
Wonderful
(13)
$460 nightly
The price is $510
$510 total
Oct 22 - Oct 23
Total with taxes and fees




Seabreeze Escape WF RV Lot 489
Seabreeze Escape WF RV Lot 489Cudjoe Key
8.0 out of 10, Very good, (1)
8.0/10
Very good
(1)
$243 nightly
The price is $261
$261 total
Oct 19 - Oct 20
Total with taxes and fees
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Top Summerland Key Hotel Reviews




Parmer's Resort
Parmer's ResortSummerland Key
10/10 Excellent
Rooms were right on the water with great views, property had some nice amenities and the boat ramp and slips were exactly what I needed. Annette at the front desk was super friendly and knows the true meaning of Customer Service. Because of her, we will be back for sure and tell all our friends, this is the place to stay!
Rooms were right on the water with great views, property had some nice amenities and the boat ramp and slips were exactly what I needed. Annette at the front desk was super friendly and knows the true meaning of Customer Service. Because of her, we will be back for sure and tell all our friends, this is the place to stay!
Michael




Sugar Loaf Lodge
Sugar Loaf LodgeSummerland Key
10/10 Excellent
Upon our arrival, the sight of 2 iguanas on the lounging on the bridge by the pristine water at the back of the property had my entire family out of the minivan at lightning speed. They followed one, which lead them to trees full of these beautiful lizards. The front desk personnel, a very amiable gentleman, was very friendly and welcoming. Our room was in the middle of the 2nd floor, and had a fantastic view of the bay. And yes, there were more iguanas looking at us from the first floor, some...
Upon our arrival, the sight of 2 iguanas on the lounging on the bridge by the pristine water at the back of the property had my entire family out of the minivan at lightning speed. They followed one, which lead them to trees full of these beautiful lizards. The front desk personnel, a very amiable gentleman, was very friendly and welcoming. Our room was in the middle of the 2nd floor, and had a fantastic view of the bay. And yes, there were more iguanas looking at us from the first floor, some...
Momi




Looe Key Reef Resort
Looe Key Reef ResortSummerland Key
10/10 Excellent
Nice place
Nice place
William




Starlight Serenity - Hideaway w Stunning Views
Starlight Serenity - Hideaway w Stunning ViewsSummerland Key
10/10 Excellent
The host team is amazing and very responsive. The house is very beautiful inside and out. We loved grilling downstairs, so much room down there. We loved our stay here because it was very secluded, unlike Key West, where you are on top of each other. The location is perfect because you can still make it down to Key West in 25 minutes for activities and food.
The host team is amazing and very responsive. The house is very beautiful inside and out. We loved grilling downstairs, so much room down there. We loved our stay here because it was very secluded, unlike Key West, where you are on top of each other. The location is perfect because you can still make it down to Key West in 25 minutes for activities and food.
max




Almond Tree Inn Hotel - Adults Only
Almond Tree Inn Hotel - Adults OnlyOld Town Key West
10/10 Excellent
The service was over the top! From the front desk to the cleaning staff, everyone was friendly and always looking to do more. Room and hotel had a boutique feel that you don't see with the chain hotels. Also the location is ideal. One block off the action. Duval street is loud and crazy, but turn into the hotel and it suddenly becomes quite and comfortable. We will definitely be back
The service was over the top! From the front desk to the cleaning staff, everyone was friendly and always looking to do more. Room and hotel had a boutique feel that you don't see with the chain hotels. Also the location is ideal. One block off the action. Duval street is loud and crazy, but turn into the hotel and it suddenly becomes quite and comfortable. We will definitely be back
william




Simonton Court Historic Inn & Cottages
Simonton Court Historic Inn & CottagesKey West Historic District
10/10 Excellent
The room was clean and neat, everyone is very friendly and helpful. So glad we booked this place last minute. The best time we've ever had in Key west. You will not get anything more authentic than this place. Loved it!
The room was clean and neat, everyone is very friendly and helpful. So glad we booked this place last minute. The best time we've ever had in Key west. You will not get anything more authentic than this place. Loved it!
RADANA




Douglas House - Adults Only
Douglas House - Adults OnlyOld Town Key West
10/10 Excellent
The Douglas House served as a perfect home base while in Key West. The location allows for easy access to all Duval has to offer. Really enjoyed being able to hear the national anthem being played every morning at 8 from the Navy base..
The Douglas House served as a perfect home base while in Key West. The location allows for easy access to all Duval has to offer. Really enjoyed being able to hear the national anthem being played every morning at 8 from the Navy base..
Anthony




Artist House Key West
Artist House Key WestKey West Historic District
10/10 Excellent
Great place and location! Loved breakfast and happy hour. Convenient and pleasant service.
Great place and location! Loved breakfast and happy hour. Convenient and pleasant service.
Anonymous traveler




Orchid Key Inn - Adults Only
Orchid Key Inn - Adults OnlyOld Town Key West
10/10 Excellent
Absolutely loved our 5 night stay this past week at Orchid Key!! What a fabulous adult only boutique hotel located just steps off of Duval! We stayed in a Deluxe King the first night because we added on a night at the front end of our trip and it was just off of the pool area and very cozy. Loved the large shower and the room was so clean! Lots of fluffy towels and little extras like free waters and cookies and peppermints were left in the room. The rest of our stay was in a Deluxe King...
Absolutely loved our 5 night stay this past week at Orchid Key!! What a fabulous adult only boutique hotel located just steps off of Duval! We stayed in a Deluxe King the first night because we added on a night at the front end of our trip and it was just off of the pool area and very cozy. Loved the large shower and the room was so clean! Lots of fluffy towels and little extras like free waters and cookies and peppermints were left in the room. The rest of our stay was in a Deluxe King...
Courtney




H2O Suites - Adults Only
H2O Suites - Adults OnlyOld Town Key West
10/10 Excellent
My husband and I recently stayed at H2O Suites for 3 nights. The property was immaculate, the staff was extremely friendly and helpful, and our room was large and comfortable. We had a suite that had a plunge pool - this was amazing!! We used it several times daily. The location is perfect - one block from Duval, so everything is easily accessed, but it’s very quiet. We rented bikes from the hotel (easy parking right out back) and truly enjoyed our getaway. Cannot day enough good things about...
My husband and I recently stayed at H2O Suites for 3 nights. The property was immaculate, the staff was extremely friendly and helpful, and our room was large and comfortable. We had a suite that had a plunge pool - this was amazing!! We used it several times daily. The location is perfect - one block from Duval, so everything is easily accessed, but it’s very quiet. We rented bikes from the hotel (easy parking right out back) and truly enjoyed our getaway. Cannot day enough good things about...
Erin




Alexander's Guesthouse - Adult Exclusive
Alexander's Guesthouse - Adult ExclusiveOld Town Key West
10/10 Excellent
Absolutely wonderful destination fir a relaxing stay while in Key West. Can not say enough about the great staff— friendly, helpful, just happy to be working here. They could not be more accommodating!! Add to that complimentary wine in your room, daily happy hours by the pool, and full service cooked breakfasts that easily saves you hundreds of dollars on a 4- day stay. Can not give this place enough praise. We are already planning a return trip.
Absolutely wonderful destination fir a relaxing stay while in Key West. Can not say enough about the great staff— friendly, helpful, just happy to be working here. They could not be more accommodating!! Add to that complimentary wine in your room, daily happy hours by the pool, and full service cooked breakfasts that easily saves you hundreds of dollars on a 4- day stay. Can not give this place enough praise. We are already planning a return trip.
Dominick




The Gardens Hotel
The Gardens HotelOld Town Key West
10/10 Excellent
This was great place to stay and was in a great location. Every thing was in walking distance and was only about 100 yards off Duval Street yet on the hotel property the gardens made you feel like you were in the middle of nowhere. I would highly recommend this place and we stay there next time I am back in Key West.
This was great place to stay and was in a great location. Every thing was in walking distance and was only about 100 yards off Duval Street yet on the hotel property the gardens made you feel like you were in the middle of nowhere. I would highly recommend this place and we stay there next time I am back in Key West.
Anonymous traveler




The Conch House Heritage Inn
The Conch House Heritage InnOld Town Key West
10/10 Excellent
Check-in and Check-Out were a breeze. Very friendly staff. Breakfast was simple yet quality and ample. I would definitely stay here again and again.
Check-in and Check-Out were a breeze. Very friendly staff. Breakfast was simple yet quality and ample. I would definitely stay here again and again.
Nicholas




The Marquesa Hotel
The Marquesa HotelOld Town Key West
10/10 Excellent
We had a fine stay. Our room was secluded. That is a good description. All the little balconies had a real secluded feel. Views to the other balconies were all obscured. Staff was game on. The cafe is recognized as one of the best restaurants on the island, get a dinner reservation well in advance of your stay.
We had a fine stay. Our room was secluded. That is a good description. All the little balconies had a real secluded feel. Views to the other balconies were all obscured. Staff was game on. The cafe is recognized as one of the best restaurants on the island, get a dinner reservation well in advance of your stay.
David




Key West Villas
Key West VillasOld Town Key West
10/10 Excellent
Beautiful property and amazing owners and staff. Very kind and generous. The property is perfectly located to Duval St. and lots of bars and restaurants. The pool is heated to a perfect temperature. The rooms are beautifully appointed and large. Just be aware that this is not an adult only property, so children can be a factor.
Beautiful property and amazing owners and staff. Very kind and generous. The property is perfectly located to Duval St. and lots of bars and restaurants. The pool is heated to a perfect temperature. The rooms are beautifully appointed and large. Just be aware that this is not an adult only property, so children can be a factor.
Thys




Hyatt Vacation Club at Windward Pointe, Key West
Hyatt Vacation Club at Windward Pointe, Key WestKey West
10/10 Excellent
This was perfect for our family. We brought nanny, and got the two bedroom. Our young girls slept on the pull out couch. Pool is beautiful, cute bar. No beach… the pictures on the website trick you into thinking beach is right there. They also don’t clean your room everyday.
This was perfect for our family. We brought nanny, and got the two bedroom. Our young girls slept on the pull out couch. Pool is beautiful, cute bar. No beach… the pictures on the website trick you into thinking beach is right there. They also don’t clean your room everyday.
Lindsay




The Grand Guesthouse
The Grand GuesthouseOld Town Key West
10/10 Excellent
The Grand Guesthouse is a gem in Key West! The host was outstanding and the facility was lovely. Breakfast was simple but nice, and the Happy Hour was an added bonus. We had a nice suite- a bedroom and a living/kitchen area.
The room was nicely appointed and it was straightened by the staff each day. The room was very clean! Overall, my wife and I were impressed!
Two small improvements... the mattress was too firm. Also, the wifi was not strong enough in our room to stream anything. ...
The Grand Guesthouse is a gem in Key West! The host was outstanding and the facility was lovely. Breakfast was simple but nice, and the Happy Hour was an added bonus. We had a nice suite- a bedroom and a living/kitchen area.
The room was nicely appointed and it was straightened by the staff each day. The room was very clean! Overall, my wife and I were impressed!
Two small improvements... the mattress was too firm. Also, the wifi was not strong enough in our room to stream anything. ...
Anonymous traveler




Duval House
Duval HouseOld Town Key West
10/10 Excellent
The Duval House was absolutely precious. The garden courtyard was beautifully taken care of with plenty of nooks to sit in. The pool is mostly shaded for the hottest part of the day, which seemed especially valuable in comparison to other BnBs. Our room was very comfortable with probably the best bed I’ve been in at a hotel or BnB. And all of the staff was very responsive, friendly, and helpful. Even KissKiss, the property cat, made the rounds to our room to make sure everything was in perfect...
The Duval House was absolutely precious. The garden courtyard was beautifully taken care of with plenty of nooks to sit in. The pool is mostly shaded for the hottest part of the day, which seemed especially valuable in comparison to other BnBs. Our room was very comfortable with probably the best bed I’ve been in at a hotel or BnB. And all of the staff was very responsive, friendly, and helpful. Even KissKiss, the property cat, made the rounds to our room to make sure everything was in perfect...
Sarah
